BOBBYCAST #650 - Debating the Best Country Crossover Hits into Pop

Summary

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Podcast Summary: Bobbycast #650

Episode: Debating the Best Country Crossover Hits into Pop
Host: Bobby Bones with Eddie, Mike, and Brandon Ray
Date: August 6, 2026

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Overview

In this lively "Bobbycast" episode, Bobby Bones and co-hosts Eddie and Mike are joined by singer-songwriter Brandon Ray for a spirited debate and draft: What are the best country songs that crossed over into the pop charts? The group takes turns selecting songs, shares insider stories from Nashville, breaks down the mechanics of crossover success, and ultimately goes to three AIs (ChatGPT, Gemini, Claude) to crown a winner. The episode mixes banter, chart talk, and fan perspectives with fun personal anecdotes.

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Key Discussion Points & Insights

Introductions & Format (02:00–03:50)

• Bobby Bones introduces the roundtable: himself, Eddie (his bandmate and Bobby Bones Show regular), and Brandon Ray (songwriter and creative lead).
• The Premise: Each participant drafts four (later five) country songs that successfully crossed into pop, with the winner decided by AI rankings.
• Brandon Ray: “We’ll have three different AIs at the end to judge—Gemini, ChatGPT, and Claude. And we’re not paid by big AI!” (04:00)

Drafting Begins: Iconic Crossovers (04:18–12:10)

Round 1

• Brandon (as Kenny): Picks Faith Hill – “Breathe”
  • “That’s good. I wasn’t going back that far.”
    —Brandon Ray (04:27)
• Conversation about Taylor Swift’s varying levels of crossover, debate about what counts as a true crossover hit.

Round 2

• Brandon (changing his mind): “Islands in the Stream" by Kenny Rogers & Dolly Parton

  • “I got to go Kenny and Dolly – ‘Islands in the Stream.’ Written by Barry Gibb of the Bee Gees, by the way.” (06:00–07:02)
  • Fun debate over who wrote the song, with misdirects involving Barry Manilow.

• Mike: Selects Taylor Swift – “Mean”

  • “Did it cross over, though?” —Brandon Ray questions the chart performance. (08:38)
  • Mike argues “Mean” straddled the country-pop line.

Round 3

• Brandon (as Kenny): Lady Antebellum – “Need You Now”
  • “That was a mum monster.” (09:27)
  • Insider story: Song almost wasn’t even a single; label/promotion mechanics behind country-to-pop crossovers.
    —“It’s all a money thing... The label has to commit to do the promotion for pop. It takes a lot of money.” (10:31–10:58)
• Brandon (as himself): Rascal Flatts – “Bless the Broken Road”

Round 4

• Mike: Willie Nelson & Julio Iglesias – “To All the Girls I’ve Loved Before”
  • “That’s a huge crossover hit.” (14:40)

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Taylor Swift Dilemma & Genre Blending (15:59–16:30)

• Discussion: Difficulty pinpointing which Taylor songs had genuine pop crossover versus country fame.

  • “I don’t know on Taylor songs what crossed. That’s why I’m so confused. It’s a great song, and probably was.” —Brandon Ray on “Love Story” (16:16)

• Brandon: Johnny Cash – “Ring of Fire” (19:37)

  • Questions over whether it actually hit the pop charts; discussed as a culturally massive record.

• Mike: Dolly Parton – “9 to 5”

  • “That’s a great pick...I would have double dollied if I thought of that.” – Brandon Ray, on Dolly's pop appeal and production trivia (21:32)

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Rounds Continue: Recent Hits and Personal Stories (22:44–30:43)

• Kenny: Ella Langley – “Choosing Texas”

  • "That just happened yesterday ... but it was a number one Billboard song for a while.” (23:07)

• Brandon: Story of crossover songs frustrating Nashville insiders when they hit pop much later:
  “...when a song would blow up within our format and then would cross over and people would go like, ‘Oh, we’ve discovered this song.’ And we’re like, we’ve had that song for a year and a half.” (24:31)

• Brandon: Lone Star – “Amazed”

  • Last minute realization, declared the most obvious yet overlooked pick:
    “I did 10 episodes on every single year. ...I thought about Lone Star ‘Amazed.’ That’s the home run.” (29:45–30:06)

• Mike: Shania Twain – “Man! I Feel Like A Woman!”

  • Group realizes major omission: “I feel like we really messed up by not putting Shania Twain on there.” (30:46)

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Overtime / Bonus Round: More Crossover Contenders (31:17–39:04)

• Discussion of Chris Stapleton – “Tennessee Whiskey” (32:28)
• Discussion of Florida Georgia Line (FGL) & Nelly – “Cruise” Remix (28:46, 34:33)
• Rascal Flatts – “Life Is a Highway” added by Brandon (39:04)
• Kenny Rogers – “The Gambler” and Willie Nelson – “On The Road Again” also floated as crossover picks (39:10)

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AI Deliberation & Results (41:03–49:20)

• Rankings sourced from three AIs based on Billboard Hot 100/pop chart success.
• Notable Quotes:
  • “Mean didn’t reach pop top 40. Willie Nelson didn’t reach pop top 40. ...Dolly Parton hit number one. Shania Twain 23. Cruz four on both!” —Brandon reading AI results (43:24–43:54)
  • “Brandon’s got the best team and he’s still got a song climbing while everyone else is playing with history.” —Claude AI verdict (47:13)
  • “Your nine to five and Cruz, wow — that’s crazy.” —AI summary feedback to Eddie (43:54)

Final AI Rankings:

1. Brandon (Faith Hill “Breathe”, Lady A “Need You Now”, Taylor Swift “Love Story”, Ella Langley “Choosing Texas”, Chris Stapleton “Tennessee Whiskey”)
2. Bobby/Mike (Kenny & Dolly “Islands in the Stream”, Rascal Flatts “Bless the Broken Road”, Johnny Cash “Ring of Fire”, Lone Star “Amazed”, Rascal Flatts “Life is a Highway”)
3. Eddie (Taylor Swift “Mean”, Willie/Julio “To All the Girls I’ve Loved Before”, Dolly Parton “9 to 5”, Shania Twain “Man! I Feel Like A Woman!”, FGL/Nelly “Cruise”)

Fun Stats:

• Discussion about which Taylor Swift songs were the true biggest crossovers (“Love Story”, “You Belong With Me”).
• Hot 100 peak numbers cited by AI for nearly every pick.
• Notable Omission: Group jokes about missing out on mega-hits from Garth Brooks, Leann Rimes, and others.

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Notable Quotes & Memorable Moments

• On the challenge of identifying true crossovers:

  • “Did it just get really popular later to everybody or did it actually cross over?” —Brandon Ray (05:06)
  • “If you take the charts out of it ... culturally impactful.” —Kenny (50:10)

• On the mechanics of crossover:

  • “It’s a label has to commit…it just takes a lot of money to promote a record anyway.” —Brandon Ray (10:58)

• On Honorable Mentions and near misses:

  • “We really messed up by not putting Shania Twain on there.” —Mike (30:46)
  • “Johnny Cash, Ring of Fire: feels more like an all-time classic than a Crossover pop hit.” —Claude AI (44:49)

• Humorous banter and rapid-fire self-deprecation:

  • “You kicked our butts—and Eddie’s sucking again. And then every time, claims, no, I’ve won before and never has won.” —Brandon Ray (51:25)
  • “You work for Halloween. So let’s not act like there’s no personal bias here.” —Brandon Ray, teasing “To All the Girls” pick (51:54)

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Timestamps for Key Segments

| Segment | Timestamps | |:------------------------------------|:-----------------:| | Introductions & Format | 02:00–03:50 | | First Draft Picks | 04:18–12:10 | | Taylor Swift Crossovers Debate | 15:59–16:30 | | Mechanics of Country-Pop Crossover | 10:31–11:42 | | Rascal Flatts “Bless the Broken Road”| 13:08–13:56 | | Jokes & Stories about Halloween, Costumes | 14:40–15:28 | | Bonus Round / Overtime Picks | 31:17–39:04 | | Recap and AI-Based Winner Selection | 41:03–49:20 | | Discussion: “What Would Be the Best Taylor Song?” | 49:47–51:13 | | Reflections on Crossover Metrics & Culturally Impactful vs. Chart Hits | 50:10–51:13 |

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Takeaways

• Brandon Ray’s list dominated based on data (chart rankings), highlighted by both classics and an ultramodern hit (“Choosing Texas”).
• Taylor Swift’s impact and the fuzzy lines of crossover success led to the longest and most recurring debate.
• AI verdicts aligned, using actual Hot 100 numbers, bringing the conversation full circle to data rather than gut feeling or memory.
• Participants found that cultural impact sometimes differs from what charts “prove.”
• Fun, irreverent banter and personal stories provided the episode’s signature character.

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Share this episode if you love country-pop collisions and hearing music nerds argue!

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Transcript

[Podcast Host / Announcer]

This is an iHeart podcast. Guaranteed Human

[Bobby Bones]

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[Brandon Ray]

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[Podcast Host / Announcer]

What do I do?

[T-Mobile Representative]

Well, there are 250 reasons to join T Mobile.

[Eddie]

Like what?

[T-Mobile Representative]

You can keep your phone and your number and T Mobile helps pay it off up to $800 per line.

[Brandon Ray]

So I wouldn't have to buy a new phone?

[T-Mobile Representative]

Yep. Plus your plan price stays the same for 5 years on experience plans. Nice. Find your reason@t mobile.com

[Advertisement Voice]

via virtual prepaid guard card. Typically takes 15 days after rebate submission price guarantee on Talk text and 5G data exclusions like taxes and fees.

[Amazon Health AI / Advertisement Voice]

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[Narrator / Personal Storyteller]

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[Amazon Health AI / Advertisement Voice]

Don't go down the rabbit hole. Amazon Health AI gets you the right care fast. Healthcare just got less painful.

[Reese Witherspoon (Advertisement Voice)]

Reese Witherspoon here, checking into my favorite hotel in Paris.

[Brandon Ray]

Bonjour. Bonjour.

[Reese Witherspoon (Advertisement Voice)]

I'm traveling with my Wells Fargo Autograph Journey card. So I earn rewards wherever I book. Travel five times points with hotels, four times with airlines, three times on restaurants and other travel and one point on other purchases. Phew, that was a lot. I need to lie down.

[Bobby Bones]

Is the room ready?

[Brandon Ray]

Visit Wells Fargo.com autographjourney Terms apply. Welcome to another great debate where we don't know what we're gonna talk about. There's three of us here. Mike will pitch us and then we'll just start arguing about crap. I'm Bobby Bones. I don't know, what do I do? Tell jokes, do a radio show, do podcasts, written a couple books. This is Eddie. Eddie is not only half of our comedy band, the Raging Idiots. He's also on the Bobby Bones Show. Wonderful dad of four. This is wonderful.

[Mike]

Thank you.

[Brandon Ray]

This is Brandon Ray. Brandon Ray is a extremely talented singer songwriter. He is the head of creative here on this project on Netflix. He does a bunch of songs end up in commercials all over. He's awesome. He's written with a lot of people in town, too, so he always adds that perspective. So here we go. We don't know what we're about to discuss and argue about. Mike will tell us now.

[Eddie]

We'll be debating the best country crossover hits into pop.

[Mike]

Okay.

[Brandon Ray]

And as always, we will spin the wheel first to see who goes first. And we'll all have four spots to draft best country songs that ended up being pop songs, man. Okay, let's spin it up. We got all three of us on the wheel here. Is there any fact checking on this?

[Eddie]

You can do that.

[Mike]

What would be the fact?

[Brandon Ray]

I don't know. But you could say every Taylor Swift song.

[Narrator / Personal Storyteller]

Right.

[Brandon Ray]

But I don't know.

[Mike]

That's true.

[Brandon Ray]

But that was only from, like, her early days. And then. And then we will go to three also. Brandon, you'll go first. We'll go to three different AIs at the end to settle and see who won.

[Kenny]

Right.

[Brandon Ray]

It's very fair because we don't get paid by big AI. No. So we'll go to Chad gbt. We'll go to Gemini.

[Mike]

Gemini was one of them.

[Additional Participant]

Yeah.

[Brandon Ray]

Gemini is one. Mike has.

[Advertisement Voice]

Yeah, yeah, yeah.

[Mike]

And then what was the.

[Brandon Ray]

Claude. Claude. I'm a Claude guy. So we'll put it in and then we'll have a winner. Okay. So best country crossover hits into pop. Brandon, you have the first overall pick.

[Kenny]

All right. The first one that popped into my head is by Faith Hill, and it's called Breathe.

[Brandon Ray]

That's good.

[Mike]

That is a good one.

[Brandon Ray]

That's good. I wasn't going back that far.

[Mike]

Oh, really? I started way back, like.

[Brandon Ray]

But it opens my eyes and my mind to other.

[Kenny]

Because.

[Brandon Ray]

Cause I got such a good one. Oh, man. Now I'm torn. You opened me up.

[Kenny]

Sorry.

[Brandon Ray]

You opened me up to some good ones. Okay. I'm still gonna go where my head was first. I don't know if this was the biggest one. I'm going to go.

[Mike]

How far back are you going?

[Brandon Ray]

Well, it's the 2000s.

[Mike]

Okay.

[Brandon Ray]

But it's the whole debate of. And AI is going to settle this for us.

[Kenny]

That's true.

[Brandon Ray]

Like, did it just get really popular later to everybody or did it actually cross over? And most. I'm talking about Taylor Swift.

[Kenny]

Oh, okay.

[Brandon Ray]

Because her songs now, everybody loves all of them. But for example, Tim McGraw didn't really cross over.

[Mike]

No, it didn't.

[Brandon Ray]

Like, it probably had a little dance.

[Podcast Host / Announcer]

Yeah.

[Brandon Ray]

But it didn't really cross over. So if I'm gonna go with a Taylor song.

[Mike]

So you Thinking Early Taylor.

[Brandon Ray]

No, I have to think mid Taylor,

[Mike]

because that's when it really was processing.

[Brandon Ray]

Because Late Taylor was pop.

[Mike]

Yes.

[Kenny]

Right.

[Mike]

Once you get to the Red Album,

[Brandon Ray]

you can't do well. Some of the Red Album, though, was cross. That's the album, let's say.

[Kenny]

Is it the Red Album?

[Brandon Ray]

That's the album.

[Mike]

Interesting.

[Brandon Ray]

I'm gonna go, Kenny. And Dolly Islands in the Stream.

[Mike]

You said you were gonna go.

[Brandon Ray]

I know, but I did.

[Mike]

Like, that's what I was gonna do.

[Brandon Ray]

But I couldn't decide on which Taylor won. And since I was, like, judging us.

[Mike]

That's so rude.

[T-Mobile Advertisement Voice]

Yeah.

[Mike]

You said you were going Taylor.

[Brandon Ray]

I was, but then I changed my mind last minute.

[Mike]

My goodness.

[Brandon Ray]

Because I wouldn't have fed you all the Taylor talk if I didn't mean it. I just. I just couldn't commit because I didn't know which one did what.

[Mike]

Dude, now I don't know what to do with my life.

[Brandon Ray]

And if this was a voting thing, I think I would have gone Taylor because I would have pandered. But since AI is judging us, I got to go. Kenny. Dolly Islands in Stream, which, by the way, written by

[Mike]

Willie.

[Eddie]

I know that.

[Mike]

I feel like everything was written by Willy. Islands in the Stream was written by Barry Manilow.

[Brandon Ray]

No, you're close.

[Mike]

Okay, hold on, hold on. Barry White.

[Brandon Ray]

You're close. Yeah, you're the right close.

[Mike]

Like, who's saying Copacabana?

[Kenny]

That's Barry Mano.

[Mike]

Barry Manilow.

[Eddie]

Okay.

[Mike]

Oh, gosh. It's somebody like that.

[Brandon Ray]

It's not only someone like that. You've nailed a part of it.

[Mike]

Like, it's gotta be the Barry.

[Kenny]

There you go.

[Mike]

Barry Gibbs.

[Brandon Ray]

Barry Gibbs to the fan.

[Mike]

Barry Gibbs. Bee Gees.

[Brandon Ray]

The Bee Gees.

[Amazon Health AI / Advertisement Voice]

Really?

[Brandon Ray]

They wrote it and it wasn't even right. Am I thinking of that song?

[Kenny]

Wrote it and produced it.

[Brandon Ray]

I was so sure of it, I started to doubt myself because it was written for other. They tried to pitch it, like R and B.

[Eddie]

It's supposed to be for Marvin Gaye.

[Brandon Ray]

Yeah.

[Mike]

Was it not good enough to be Bee Gees? Because I feel like it'd be perfect for a Bee Gees song.

[Brandon Ray]

I didn't ask him. I don't know.

[Bobby Bones]

All right.

[Brandon Ray]

Kenny and Dolly Islands and the Strange Man. Number one pick.

[Mike]

See, and part of why I wanted you to go Taylor is because Taylor's a great pick. But Taylor, there's like, where do you go?

[Brandon Ray]

That's what. That's why I was talking it out.

[Kenny]

Like, where do you go?

[Brandon Ray]

And I never settled. It was like the End of Castaway, where you don't know where he goes.

[Mike]

Does he go left? Does he go right?

[Brandon Ray]

Does he go back to the right? There's a whole. And it just shuts down. The movie shuts down. You're like, what the crap?

[Mike]

I feel like he goes back to the girl, though. But I really don't know.

[Amazon Health AI / Advertisement Voice]

Yeah.

[Brandon Ray]

What if they do a smash cut and it's just him humping a volleyball?

[Mike]

Oh, yeah.

[Brandon Ray]

He just couldn't get it out of his mind. It's like we find out what Tom Hanks was really up to, and it's just him grinding on a ball, and he just lives his life in love for the ball.

[Kenny]

I don't want to see Castaway too.

[Mike]

It's all the relationship between him and Wilson.

[Brandon Ray]

It's just a weird documentary on a guy in love with a volleyball.

[Kenny]

Get dark.

[Mike]

Okay, all right. I'm just going have to go Taylor, and I'm going to just go and say, all right, this was probably the crossover song. Gosh. I'm going to go with Mean, Taylor.

[Brandon Ray]

Mean. I love that song. It's possibly top three Taylor Swift songs.

[Mike]

All you are is me.

[Brandon Ray]

Did it cross over, though?

[Mike]

Yeah, yeah. I believe I mean everything. There was a lot of Taylor crossover, but I feel like mean was the one where it's like, it wasn't so country.

[Brandon Ray]

I love that song. Maybe number one.

[Kenny]

I actually heard that the other day, and it reminded me, like, dude, this is a great song.

[Mike]

All you are is me.

[Brandon Ray]

It's got the band.

[Kenny]

You.

[Brandon Ray]

Yeah, yeah. I just don't know the crossover, the

[Mike]

full crossover, and it's kind of a wrist pick, but yeah.

[Brandon Ray]

Okay, Brandon, back over to you. Faith Hill. Breathe. What are you gonna add to that?

[Kenny]

All right, I would go Taylor Swift, and I probably should, but I don't want this one to be stolen. So I'm gonna say need you'd now from Lady Antebellum.

[Mike]

I had it.

[Brandon Ray]

Jam.

[Mike]

I had it. I loved that song.

[Brandon Ray]

I thought I could get that one in, like, the third round.

[Mike]

Me too.

[Brandon Ray]

But that was a mum monster.

[Kenny]

Huge.

[Mike]

Like, you were doing pop radio at

[Brandon Ray]

the time, playing the crap out of it.

[Mike]

And I remember listening to a show and when that song would come on, I'd be like, I like this one. Turn it up.

[Additional Participant]

Ding.

[Brandon Ray]

So getting to know those guys in that band, there's three of them. There's Charles, Dave, and Hillary. And even getting to know the writers of that song. That is a song that you hear a lot of times. There was a throwaway crazy that they just recorded it really wasn't even gonna make the album, much less be a single. And they're just going through music. It's one of those stories. Okay. Yeah, I think we should put it on the record.

[Eddie]

Right?

[Brandon Ray]

Huh?

[Mike]

Good thing you did.

[Brandon Ray]

Not only that, I think. I think it should be the scene. It's risky, but let's make it the single. Yeah. And then what? Yeah. Change their life.

[Kenny]

How does this decision ever.

[Mike]

How does it cross over? Like, how does it get in the hands of pop radio?

[Brandon Ray]

So I can tell you, generally speaking, because I think a lot of stories are different. If it does tremendously well at country and someone in the country space, label wise, sees an avenue for it to Also sees an avenue that they feel like is a good investment to then do promotion for it within pop. Because it's all a money thing.

[Mike]

Okay.

[Brandon Ray]

Now, occasionally you'll have stations that go, this is such a jam. We're just going to play it anyway.

[Eddie]

Rare.

[Brandon Ray]

It's a label has to commit to now doing the promotion for that record over on the pop side of things. Because that's a lot more money it takes. Just takes a lot of money to promote a record anyway.

[Mike]

Yeah, yeah, yeah. So, yeah, I didn't know if it was a radio decision, like program directors saying, like, hey, we're gonna play this also on the pop stadium.

[Brandon Ray]

Yeah, that can happen too. Where, let's say, Lady A, I'll just use that song. There could be a program director in Atlanta and this didn't happen. But at a pop station that goes, this song is doing so well in our market through research. We're also going to play it on the pop station. And then it does so well on the pop station through research that other stations go, oh, we should add it then, too. Because the research is showing it's doing well here and it can also blow up that way.

[Mike]

Yeah. Okay.

[Brandon Ray]

I would say for the most part, it is directly from the record label deciding that it's worth the money to promote it to pop radio.

[Mike]

That's got to be a risk.

[Brandon Ray]

It is. And they have a lot of data, though, because they can go, look in your city. Look how it's selling in your city or streaming in your city. So, yeah, that's it.

[Mike]

Okay.

[Brandon Ray]

But there's not a universal answer. So I don't want to be the guy that knows everything, but it's mostly a money thing. Okay, good, Good pick. Great pick.

[Mike]

That's a really good pick, Brandon.

[Brandon Ray]

Thanks, man, for my number two pick,

[Eddie]

Man.

[Kenny]

Do it. Just do it.

[Brandon Ray]

I really gotta get a Taylor song on here.

[Mike]

Yeah, you should. But I know what you're gonna do now. Talk about Taylor for 30 minutes and then pick someone else that I'm about to pick.

[Kenny]

Still his song

[Brandon Ray]

with Taylor. The Red Album for sure was her last album before she went country or went pop. But again, like our song. Did that cross over or did it just get way awesome later to everybody?

[Eddie]

Yeah.

[Mike]

I don't know. I feel like she was winning awards. Not in the country realm with all those. Wasn't she? Was she winning like American Music Awards and all kinds? Not in the country division with those songs.

[Eddie]

Okay.

[Brandon Ray]

I'm gonna go. Bless the broken road. Rascal Flies.

[Mike]

See this guy.

[Environmental Advocate / Advertisement Voice]

Wow.

[Mike]

You're never gonna pick a Taylor song. I know you. That's a good one. It's a real good one.

[Brandon Ray]

Cuz that one crossed over.

[Kenny]

Yeah.

[Mike]

Was that their crossover?

[Brandon Ray]

They.

[Eddie]

Yeah.

[Brandon Ray]

I'm not telling you anything else because they had.

[Mike]

Because I feel like there's a.

[Brandon Ray]

They've got a few bigger ones. They've got that. That was my. Because, like, the song from Cars was never supposed to be a single.

[Eddie]

Yeah, but.

[Brandon Ray]

But, but it was big. It's for sure big.

[Eddie]

Yeah.

[Brandon Ray]

So I. I thought in my head of those two and I went with Bless the Broken Road because it wasn't a cover. But it doesn't matter to people. It doesn't matter. But I did think about that.

[Mike]

Well, I'm just thinking about AI. What's AI want now?

[Brandon Ray]

You're pandering to AI.

[Kenny]

Can't pander to AI.

[Mike]

What does AI want here?

[Brandon Ray]

All right, you have Taylor Swift.

[Advertisement Voice]

Mean.

[Healthcare Advertisement Voice]

Yeah.

[Mike]

I feel like I need another Taylor song.

[Brandon Ray]

If you go all Taylor, you might win it. Have you ever won?

[Eddie]

Ever?

[Mike]

Yeah, I've won one with it.

[Eddie]

Not from AI. No.

[Kenny]

No, he's never won.

[Healthcare Advertisement Voice]

Sure.

[Brandon Ray]

Guys, I don't even think you've won a vote when we used to vote.

[Kenny]

No.

[Mike]

Huh. Okay, well, this is. I'm definitely gonna win one here. So let's go with a Willie Nelson song. It was a duet. It's Willie and Julio Iglesias with all the girls I've loved before.

[Kenny]

Oh, wow.

[Brandon Ray]

Strong.

[Mike]

That's a huge crossover hit.

[Kenny]

What year was that?

[Mike]

I don't know, dude.

[Brandon Ray]

Halloween one year. We went as that. You did? Of course. It matched our races. And so I was Julio. Obviously we race matched, so everybody relax. And I was Willie and he was Julio, and we did Natural Halloween.

[Mike]

Great.

[Healthcare Advertisement Voice]

Yeah.

[Mike]

Do we even sing? Do we sing a song?

[Brandon Ray]

Nobody really wanted us to.

[Kenny]

Was anyone able to Guess, though.

[Mike]

Probably not.

[Brandon Ray]

Yes. Because I had a red bandana on and a long. I think you could tell that I was Willie and it just was like. It just looked like Willie and his Mexican buddy.

[Mike]

Yeah.

[Eddie]

But then it.

[Brandon Ray]

If you knew, knew, you knew.

[Kenny]

Okay, okay, you got it.

[Mike]

Yeah.

[Kenny]

This is like inside, big time inside.

[Brandon Ray]

If you knew, knew, you thought it was a great costume. If you, you didn't, you were just like, what's the guy dressed up like a girl for with the pigtails with a Mexican guy.

[Healthcare Advertisement Voice]

Who's he?

[Mike]

Yeah, it was like the year, maybe two years after that I went as Benny the Jet Rodriguez, you know, from the sandlot.

[Brandon Ray]

I also went as Squintz.

[Mike]

Yes, I know. And everyone thought I was Cheech from Born in the east la.

[Brandon Ray]

And everyone kept asking me, are you yourself? As a kid, it was the same crap. No one really got us. Okay, great one. Brandon, over to you.

[Kenny]

All right, I'm gonna have to go with a Taylor Swift monster.

[Brandon Ray]

Switch it up on us and don't do it.

[Mike]

Yeah, yeah, yeah, do that.

[Kenny]

It's Reba Mac.

[Amazon Health AI / Advertisement Voice]

No, just kidding.

[Kenny]

Taylor Swift Love Story.

[Brandon Ray]

I. I don't know on Taylor songs. What? Cross. I mean, that's why I'm so confused. It's a great song and probably was.

[Mike]

I really think we can do so many Taylor songs right.

[Kenny]

This one though.

[Brandon Ray]

Are you sure it crossed over?

[Kenny]

Yeah, it might have been one of the biggest crossovers.

[Brandon Ray]

Ken, hang tight. The Bobbycast will be right back.

[T-Mobile Advertisement Voice]

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[Additional Participant]

Trip booked and switching to T mobile help make it happen with experience beyond

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[Additional Participant]

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[Additional Participant]

Exactly. Best switch I ever made.

[T-Mobile Advertisement Voice]

This is just one reason to join T Mobile this summer. There are 250 reasons. Find yours.

[Advertisement Voice]

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[Amazon Health AI / Advertisement Voice]

Allow eight weeks Amazon Health AI presents

[Podcast Host / Announcer]

painful thoughts I. I can't stop scratching my downtown.

[Bobby Bones]

Mm.

[Podcast Host / Announcer]

Yeah, but I'm not itching to go downtown and tell a receptionist I'm here to talk about my Downtown. Some things you'd rather type than say out loud.

[Amazon Health AI / Advertisement Voice]

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[Reese Witherspoon (Advertisement Voice)]

Reese Witherspoon here, checking into my favorite hotel in Paris.

[Brandon Ray]

Bonjour. Bonjour.

[Reese Witherspoon (Advertisement Voice)]

I'm traveling with my Wells Fargo autograph Journey card. So I earn rewards wherever I book. Travel five times points with hotels, four times with airlines, three times on restaurants and other travel, and one point on other purchases.

[Additional Participant]

Phew.

[Reese Witherspoon (Advertisement Voice)]

That was a lot. I need to lie down. Is the room Ready?

[Brandon Ray]

Visit wells fargo.com autographjourney Terms apply. And we're back on the Bobbycast. Have Kenny and Dolly Islands in the Stream. Have Rascal Flats. Bless the broken road. So let's think about Taylor.

[Mike]

Don't do this. Don't do this every time, but really pick one.

[Brandon Ray]

I'm gonna be really risky with this one.

[Mike]

Okay.

[Brandon Ray]

Because I feel like this is massive risk, but humongous reward wasn't alive when this song did its thing. Also wasn't alive for Islands in the Stream.

[Mike]

I don't think we might have been. I feel like that was 80s, was that early 80s, maybe 70s.

[Brandon Ray]

I'm gonna go, gosh, don't do it with a native from where I'm from, Johnny Cash.

[Mike]

Oh, okay.

[Brandon Ray]

Because there's a reason he's in both the Country Music hall of Fame and the Rock and Roll hall of Fame.

[Eddie]

Yeah.

[Brandon Ray]

It's cause dude did songs that everybody loved. And so could you pick all of

[Mike]

his songs to be crossovers?

[Brandon Ray]

It's kind of like the Taylor Swift thing.

[Eddie]

I don't know.

[Mike]

I feel like you.

[Brandon Ray]

I'm gonna. Johnny Cash. Ring of Fire.

[Mike]

That's good.

[Bobby Bones]

Wow.

[Brandon Ray]

My assumption is that that song was played everywhere.

[Kenny]

What's the rule?

[Mike]

Is the rule that it had to be played on pop radio. But I mean, like, back then, what was pop radio? Wasn't everything.

[Brandon Ray]

It was top 40.

[Mike]

Okay, so. So we should look at what, 19, whatever, ring of Fire, whatever year that was, and see if it played in top.

[Brandon Ray]

Well, AI is going to tell us because Mike's going to type in, I

[Eddie]

have an answer for you right now. If you want it.

[Brandon Ray]

Do we want it? Do we want it? Because I can't pull back. And if it's bad, I'd rather not know right now.

[Mike]

And so that's true. So if it doesn't qualify as a poop.

[Brandon Ray]

No, no. It just won't get rated high by AI.

[Mike]

Okay. All right. That's fair. I like that.

[Brandon Ray]

Yeah. Because we can ask the question.

[Kenny]

I like that.

[Mike]

Gosh.

[Brandon Ray]

We're debating best country crossover hits in the pop based on their country success and their success on the top 40 charts.

[Mike]

I would bet Ring of Fire was on the top 40 charts. I would bet.

[Brandon Ray]

I hope so. But I don't know. No, because it wasn't there.

[Mike]

I would think so.

[Brandon Ray]

Okay.

[Mike]

Eddie, man, I thought you were going to go with this. I thought you were going to go with. Until it was. Until you said where I come from. Like, I'm from my. From Arkansas. Yeah, I thought you're going to go with Dolly.

[Brandon Ray]

Oh, it's a great one.

[Mike]

So I'm going to go with great one, Dolly Parton. I even think they did a movie from this. You're freaking going, Give me Dolly. 9, 2, 5.

[Brandon Ray]

That's a great pick.

[Mike]

Let's go.

[Brandon Ray]

And I would have double dollied if I'd have thought of that.

[Mike]

Yeah, of course.

[Brandon Ray]

Cause they say never go double Dolly, but I'd have gone double Dolly. Yeah, I'd go double Dolly. Oh, what a great pick. Because that was, I would assume, a number one song on the pop charts and for sure, country charts.

[Mike]

Yeah, yeah, yeah, yeah, yeah.

[Brandon Ray]

And that at the beginning is her doing her fingernails on the microphone.

[Mike]

Did you hear that?

[Kenny]

Did you see? Really?

[Healthcare Advertisement Voice]

Yeah.

[Mike]

On the microphone.

[Brandon Ray]

She's doing her.

[Mike]

I almost thought it was a typewriter way.

[Brandon Ray]

And I think that's what it's supposed to sound, right?

[Mike]

Yeah.

[Brandon Ray]

Am I crazy?

[Mike]

Like, she's working.

[Brandon Ray]

Yeah, but she told us it was her fingernails.

[Mike]

She said that?

[Kenny]

Mind blown.

[Mike]

She's like, I use my fingernails on the mic.

[Brandon Ray]

Is that your Dolly impression?

[Mike]

I was.

[Kenny]

I liked it. It was bad.

[Mike]

No, I didn't work.

[Brandon Ray]

Dude, that is possibly your best one and could have gone in the first round.

[Mike]

Let's go, baby.

[Brandon Ray]

Have you seen the nuns podcast yet where they're just gassing each other out?

[Mike]

You've told me about.

[Kenny]

You told us about that.

[Brandon Ray]

That's what I felt like whenever I was. I was like, man, that's the greatest answer ever.

[Advertisement Voice]

Thank you so much.

[Brandon Ray]

I sure wish I would have picked that, but I didn't deserve to pick that.

[Kenny]

You're so good at drafting.

[Brandon Ray]

You're so good. Yeah.

[Mike]

Thank you.

[Brandon Ray]

You waited so long to get such a good pick.

[Mike]

You are, too. I'm surrounded by the best man.

[Brandon Ray]

Brandon, you Have Faith Hill. Breathe, lady. A need you'd now Taylor Swift Love Story. You have one more pick here and your best country crossover hits into pop. What are you thinking?

[Kenny]

My mind is so clouded, I can't really think back. So don't hate me for this. I know you're an Ella fella, but choosing Texas from Ella Langley.

[Mike]

Wow, that just happened yesterday.

[Brandon Ray]

Yeah, I wouldn't have thought about that because it was so recent, but it was a number one Billboard song for a while.

[Kenny]

Long time.

[Mike]

So that's a good pick.

[Brandon Ray]

I Hope that our AIs aren't updated. Hope it's like the version from Ella, who six months ago, didn't get the update.

[Kenny]

It's like the GPS that doesn't know

[Mike]

street was in there.

[Brandon Ray]

That's a good one.

[Kenny]

Thanks, man.

[Mike]

Interesting. Oh, interesting.

[Brandon Ray]

Because you don't like it. Say more.

[Mike]

It might be too new.

[Kenny]

It wasn't my favorite pick. I'm just.

[Mike]

You went blank.

[Brandon Ray]

It's data, though. No, it's not blank. I agree. I think it's a great pick because it was a. It was number one on both charts.

[Mike]

But the picker is even, like, doubting if it was a great pick.

[Brandon Ray]

Only because it was so recent.

[Kenny]

I'm doubting. I think it was a great pick. I'm disappointed that I couldn't think of, you know, like, Islands in the Stream. That's. That's a classic.

[Eddie]

Yeah.

[Kenny]

You know, so it's just.

[Mike]

Yeah, Yeah. I mean, Ella just. That just happened. So to me, it's like, all right, let's see if AI registers it. Okay.

[Brandon Ray]

I have Kenny and Dolly Island Stream.

[Kenny]

Hello.

[Additional Participant]

Who?

[Brandon Ray]

Rascal Flats, Bust a Broken Road, Johnny Cash, Ring of Fire. If I were gonna talk through crossover songs, because I would always get a little irritated, too, because I've been in Nashville for 2013.

[Mike]

Yeah.

[Brandon Ray]

So that would be 13 years.

[Mike]

Yeah, that's right.

[Brandon Ray]

And so when a song would blow up within our format and then would cross over and people would go like, oh, we've discovered this song. And we're like, we've had that song for a year and a half. I got it. You know? Well. Territorial.

[Eddie]

Yeah.

[Mike]

Just rubs you the wrong way.

[Brandon Ray]

Yeah. Yeah. So I'm trying to think of the songs that kind of pissed me off when they would go. They'd cross over.

[Mike]

Yes.

[Kenny]

I just thought. I just thought of a monster.

[Mike]

Are you done? He's done.

[Kenny]

I'm done. I. I can't.

[Brandon Ray]

Is okay. I can't even take any hints, can we? But, like, I'm not picking this song. Because it never.

[Mike]

Why are you then go with Taylor, dude.

[Brandon Ray]

Well, hold on. A song like a Sam Hunt Body like a Back Road, did like a mid success crossover.

[Kenny]

That's a good example.

[Mike]

Yeah. Okay.

[Brandon Ray]

And I remember people being like this Sam Hunt guy, brand new, he's so good. And I'm like, shut up. He's been over here for four years.

[Mike]

Loving the back of the truck with the potatoes.

[Brandon Ray]

So my mind goes. Let me think of all those songs that made me mad.

[Eddie]

Okay.

[Brandon Ray]

And I think there's only been three or four big ones since we've been here in 13 or 14 years. Most recently Ella Langley. Choosing Texas.

[Eddie]

Right.

[Brandon Ray]

And yes. Even Morgan Wallen.

[Eddie]

Ooh.

[Brandon Ray]

As big as he is, I don't think he's had a Billboard number one.

[Mike]

I don't think so either.

[Kenny]

And can. Can you gravitate toward one song? Like that song was. Was the one with Morgan Wallen?

[Brandon Ray]

You know, I think he may have had a top five and I'm not sure which one because they all kind of sound the same. And that's all I'm saying. Yeah. I don't know. I'm going to go, man, this is such a stupid pick.

[Mike]

Why?

[Brandon Ray]

What do you say?

[Eddie]

He does have number ones on Billboard.

[Brandon Ray]

Oh, on the Hot 100.

[Additional Participant]

Oh, wow.

[Brandon Ray]

Then why was his producer, Charlie Hanselm talking about. He wants him to get a number one song finally on the pop chart.

[Kenny]

How long ago did you have Charlie on?

[Brandon Ray]

No, this was an article like last week.

[Kenny]

Oh, really?

[Brandon Ray]

Charlie Hansom was talking with, I think the Country Music hall of Fame. And he's like, my goal is to get Morgan Wallen a number one song in the pop world. We're going to do more pop stuff.

[Kenny]

Oh, maybe. I mean, I know he had number one on the like digital.

[Brandon Ray]

Yeah.

[Additional Participant]

Was it the.

[Kenny]

Was it the hot 100 mic?

[Brandon Ray]

You know what, it doesn't matter. I'm sure it was.

[Eddie]

And in the end, are you saying with no features?

[Brandon Ray]

Oh, is that what it is?

[Eddie]

Number ones are her features.

[Mike]

Oh, I have some help. Post Malone.

[Kenny]

Okay.

[Brandon Ray]

Was that a Morgan or a Post song?

[Eddie]

That was a Post Malone song.

[Brandon Ray]

So that's even really count as a Morgan number one. I get to. But he produced that for Post Malone and he produces Morgan Wallen, so. Yeah. So Morgan Wallen maybe doesn't have a number one. That's his own song, according to Charlie Handsome.

[Eddie]

Yeah. He wants him to have a number one song with no features.

[Amazon Health AI / Advertisement Voice]

Oh,

[Mike]

dude, I can think of two monsters.

[Brandon Ray]

I can think of a monster right now. That was right before we got here.

[Mike]

Then do it.

[Brandon Ray]

I just don't know.

[Kenny]

I wish I could go back in time. You can't. I truly wish I could. Because this one is the number one song ever.

[Mike]

Yeah, I think I have that one.

[Brandon Ray]

To cross over.

[Mike]

I think I have it.

[Kenny]

I think so.

[Mike]

Like, dude. Like, dude. No question.

[Brandon Ray]

Well, now I'm playing the game in my head. I'm just trying to identify what you guys are talking about.

[Mike]

Go make your pick.

[Additional Participant]

Yeah.

[Brandon Ray]

Did Michael Jackson ever do a country record?

[Mike]

Elvis. Oh, I didn't think about.

[Kenny]

Oh, don't give him.

[Brandon Ray]

Well, I thought Elvis when we talked about people in the country and rock hall of fames and gospel, because he's in all those.

[Mike]

But can I remind you, you have not picked Taylor yet. I know that's pretty good.

[Brandon Ray]

I'm just not sure enough of what her crossovers were.

[Mike]

But take your pick.

[Brandon Ray]

So you have one that's really good.

[Mike]

Really good. And I even have a backup that is a minus.

[Brandon Ray]

So I want. Can I just talk it out a little bit? And you may still want to them and I don't care. You can just steal one of them. FGL and Nelly, when they did Cruise.

[Mike]

Oh, that was legit.

[Kenny]

That's a good one.

[Mike]

But wasn't Cruise a crossover?

[Brandon Ray]

That's what I'm saying.

[Kenny]

Yeah.

[Mike]

Without Nelly?

[Brandon Ray]

Well, when they went pop, they put Nelly. So it'd be.

[Mike]

That's what it was.

[Brandon Ray]

It'd be Cruz.

[Mike]

Okay.

[Brandon Ray]

Florida Georgia Line.

[Mike]

That's not what I was thinking.

[Brandon Ray]

No. Okay.

[Kenny]

It's a really good one.

[Mike]

But that is good.

[Brandon Ray]

Oh, but you're talking down to me right now, and I don't like it. No, I don't like it.

[Kenny]

That is an okay pick.

[Mike]

I have, like, the perfect bet in my pocket right now.

[Brandon Ray]

There's also the Nelly. Tim Graw song was a Nelly song

[Mike]

over and over and. And all in my head. That one.

[Brandon Ray]

Yeah. And that was an amazing song.

[Kenny]

Yeah, go with that one.

[Brandon Ray]

But that's not a country to pop.

[Kenny]

Probably the winner.

[Mike]

Yeah, dude, you should pick that one.

[Brandon Ray]

And if we go back to the 80s and 90s, like, Garth didn't really cross over. I mean, yeah, he had songs that ended up hitting the chart, but I'm gonna go. Lone Star amazed.

[Eddie]

Wow.

[Kenny]

That's it. I didn't even think of that one.

[Mike]

You had it the whole time. You had it. No, you had the whole time.

[Brandon Ray]

I didn't have it the whole time. Yes, you did. I didn't have it the whole time. But when I started going. Because I've recorded a whole series on 90s country. And I did 10 episodes on every single year. And I went back in as I was doing cards and I thought about Lone Star amazed. Is that what you were thinking?

[Eddie]

Y.

[Mike]

That's the home run. And then I look at my stupid list and I have Taylor Swift mean as number one. That's crazy. Like all three of us.

[Brandon Ray]

That Lone Star on maze is the last minute came to me as I was talking it out.

[Mike]

Dude, that is the biggest steal of this pick.

[Brandon Ray]

Were you thinking that, Mike?

[Eddie]

I was thinking that one.

[Brandon Ray]

Yeah.

[Kenny]

That is not the one. I was thinking.

[Brandon Ray]

Do you still have a monster?

[Kenny]

I have a monster.

[Mike]

I also have an A minus.

[Brandon Ray]

Okay, go ahead.

[Mike]

And that's just because you took a maze dude like that. I felt like I was sitting on gold there.

[Brandon Ray]

You were. Cause I didn't have it.

[Mike]

And you just stole it. Okay, but I feel like we really messed up by not putting Shania Twain on there.

[Brandon Ray]

Oh my God. So that's the ultimate.

[Mike]

Is that not what you're thinking?

[Brandon Ray]

I'm so stupid.

[Mike]

How does he have a bigger one than Shania after a maze?

[Brandon Ray]

The fact that I can't. That I hate me for not looking up Shania.

[Mike]

Hey, no, don't do that.

[Brandon Ray]

Oh my God.

[Kenny]

Don't talk about my friend like that.

[Brandon Ray]

Dude, you're so right. You might win it with that one.

[Mike]

I don't know. I don't know. I'm gonna go with. Man, I feel like a woman.

[Brandon Ray]

Great one. I probably. If I were you. Wanna go one more round?

[Kenny]

Yeah, I sure do. I would love one more round. Maybe honorable mention.

[Brandon Ray]

You'd love one more round?

[Eddie]

I think one more round.

[Mike]

Mike, you gotta end it. Cause he's got. He's got gold.

[Eddie]

But I think you all are sitting on one now.

[Mike]

No, I just spit it all.

[Brandon Ray]

You have time with Nelly.

[Bobby Bones]

Eddie.

[Eddie]

Your team just got good.

[T-Mobile Advertisement Voice]

Yeah.

[Brandon Ray]

Eddie's finally competitive in the game.

[Eddie]

Your last two picks.

[Mike]

But I'm happy.

[Eddie]

Get one more great pick. You could have a chance to win.

[Mike]

But I can also have a throwaway pick.

[Kenny]

It might. It might come to you, dude. Let's vote.

[Brandon Ray]

Let's vote. Who wants to go one more round?

[Eddie]

I.

[Brandon Ray]

Okay. Me.

[Mike]

No. Mike. No.

[Eddie]

I say yes.

[Brandon Ray]

3.

[Eddie]

1.

[Kenny]

Okay.

[Brandon Ray]

Okay. Brandon, what is it?

[Mike]

Dude, you get your chance.

[Kenny]

This came to me because you said. I'm trying to think of the songs that went huge after I moved here. And you said that. And I was like, oh, my God. This song is a cover by one of the greatest singers ever.

[Brandon Ray]

I like the game. I'm trying to figure it out. Keep going.

[Mike]

One of the greatest singers ever.

[Kenny]

One of the greatest. He's one of my favorite singers. He.

[Brandon Ray]

Oh, Stapleton.

[Kenny]

Chris Stapleton. Tennessee Whiskey.

[Brandon Ray]

You know, that's a good one. But you put that as you were acting like that was the king dingling.

[Kenny]

Yeah, it's King. No, it's King.

[Mike]

It's a great song.

[Brandon Ray]

It's in the awesome.

[Kenny]

Let's just wait and see what I AI says.

[Mike]

I don't care what you guys do.

[Kenny]

I don't care. Come on, Claude, give it to me.

[Brandon Ray]

I wonder if Tennessee Whiskey crossed over, though, on the pop charts. Was it ever played on pop radio? I was here, so I don't know, but you're probably right. You sure sold that. I thought he had the one. What are you. What are you staring at?

[Mike]

I'm just trying to think, man. I'm so mad that we're going another round. It's like. It's like I just hit a grand slam and I thought I won the game.

[Kenny]

Oh, you came back.

[Brandon Ray]

Yeah, I don't think you.

[Mike]

With my four picks, I think a maze could have gotten me.

[Brandon Ray]

I don't think you would have won, actually. I was doing you a charity favor by extending it.

[Kenny]

Right.

[Mike]

No, you weren't.

[Kenny]

Absolutely.

[Brandon Ray]

You first two, as good songs as they are, they're not gonna win this. Okay, but we.

[Eddie]

No, you know what?

[Brandon Ray]

We can delete Brandon's now that you see it. No, I don't think. I don't think Brandon's Tennessee Whiskey is as good as he was building it up. I could be wrong.

[Mike]

You're right.

[Brandon Ray]

But didn't you also go?

[Mike]

Oh, yeah.

[Brandon Ray]

When he said that. Yeah.

[Mike]

That's not what I expected.

[Kenny]

You're probably right.

[Mike]

Go ahead, go. Go with your fifth.

[Brandon Ray]

Well, I don't really have one yet. I'm just saying we could back off.

[Mike]

Is that why you.

[Brandon Ray]

I've got like three. I always have. FGL and Nelly. I've cruised.

[Mike]

I know. I mean, that's the only thing I'm thinking of.

[Eddie]

But.

[Mike]

Hey, can I remind you, you haven't gone Taylor.

[Brandon Ray]

It's a good point.

[Kenny]

Guys, if you want to. If you want to back off, we can back off.

[Mike]

No, we're here already.

[Brandon Ray]

No, no, no.

[Mike]

We already hit the road. Might as well finish the race.

[Amazon Health AI / Advertisement Voice]

Hang tight.

[Brandon Ray]

The Bobbycast will be right back

[T-Mobile Advertisement Voice]

this summer. There are 250 reasons to join T Mobile, girls.

[Additional Participant]

Trip booked and switching to T Mobile. Help make it happen with experience beyond

[T-Mobile Advertisement Voice]

switch and get $100 back plus $650 in value in built in plan benefits. That's $750 in your first year guaranteed.

[Additional Participant]

And honestly, that hundred dollars back, I'm putting it towards the zipline now.

[T-Mobile Advertisement Voice]

That's how you do summer.

[Additional Participant]

Exactly. Best switch I ever made.

[T-Mobile Advertisement Voice]

This is just one reason to join T Mobile this summer. There are 250 reasons. Find yours.

[Advertisement Voice]

Savings based on the value of benefits included with experience beyond like entertainment and one year of AAA Classic and DashPass on US benefits may require activation. See plan for details. Get $100 via virtual prepaid MasterCard with eligible ported, no cash access and expires in six months. Issued by Sunrise Banks and a member FDIC.

[Amazon Health AI / Advertisement Voice]

Allow eight weeks Amazon Health AI presents

[Narrator / Personal Storyteller]

painful thoughts why did I search the Internet for answers to my cold sore problem? Now I'm stuck down a rabbit hole filled with images of alarmingly graphic source in various stages of ooze. I can clear my search history, but I can never unsee that.

[Amazon Health AI / Advertisement Voice]

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[Reese Witherspoon (Advertisement Voice)]

Reece Witherspoon here, checking into my favorite hotel in Paris.

[Additional Participant]

Bonjour.

[Brandon Ray]

Bonjour.

[Reese Witherspoon (Advertisement Voice)]

I'm traveling with my Wells Fargo Autograph Journey card. So I earn rewards wherever I book travel five times points with hotels, four times with airlines, three times on restaurants and other travel, and one point on other purchases.

[Additional Participant]

Phew.

[Reese Witherspoon (Advertisement Voice)]

That was a lot. I need to lie down. Is the room ready?

[Brandon Ray]

Visit Wells Fargo.com autographjourney Terms apply. And we're back on the bobbycast. I'm gonna go. I'm not cheating.

[Mike]

I'm not cheating.

[Brandon Ray]

I know. I'm just saying I'm not cheating.

[Mike]

Cheating heart.

[Brandon Ray]

No, I'm just saying I'm not cheating by what I'm about to do.

[Mike]

What are you doing?

[Kenny]

Oh, I thought you were referring to a song.

[Brandon Ray]

No, that's not it.

[Mike]

Did somebody put the wrong name of the song?

[Brandon Ray]

No, no. That'd be so cold. That'd be a dick move for sure.

[Mike]

Oh, you're not.

[Additional Participant]

Oh.

[Mike]

Oh, you want to pick another? Yeah, I got you. I got You. I know where you're going, and that's pretty solid. So, like, really solid. I kind of did that, right? No, I didn't. I could do that with mine.

[Brandon Ray]

You could, and it's obvious. Obviously. Mine. I mean, it's.

[Mike]

Tell you what. You do it, I'll do it.

[Brandon Ray]

You gonna say who the person is? Yes. 1, 2, 3, 4.

[Mike]

Kenny Rogers. It's.

[Eddie]

Yes.

[Kenny]

I was thinking what you were thinking.

[Brandon Ray]

Yeah, the Gambler.

[Mike]

Yeah.

[Kenny]

Wait, no, I was thinking Dolly. Nevermind.

[Mike]

I was thinking the Gambler.

[Brandon Ray]

I was thinking Shania.

[Mike]

Shania. Just different song.

[Brandon Ray]

So, like, from this moment.

[Mike]

From this moment or. I don't think that was it. I mean, yeah, it counts for sure,

[Brandon Ray]

but, man, I feel like a woman. Yeah, from this moment. What else you got?

[Kenny]

Come on over.

[Additional Participant]

No.

[Brandon Ray]

Nah, that was too country. Yeah, that's too early.

[Mike]

Okay, so you're Brad Pitt.

[Kenny]

That don't impress me much.

[Brandon Ray]

Did that go, Bob?

[Mike]

Yeah, you could do that.

[Brandon Ray]

Okay, I'm gonna go. Good point. I'm gonna go. Life is a highway. Rascal Flats.

[Mike]

You're so stupid.

[Brandon Ray]

I got two Rascal Flats.

[Mike]

Yeah, that. That might hurt you, but it might be great. Eddie, man, now I feel like I have too many options, dude. I started this fifth pick with, like, I've got nothing. Now I'm thinking, do I go Kenny Rogers, the Gambler. Massive song.

[Brandon Ray]

I mean, they made a television show after the song. Yeah, that rarely happens.

[Mike]

And then how many people when you're playing poker are like, ooh, you got to know when to hold?

[Brandon Ray]

Not many. And I played a lot of poker for a lot of time.

[Mike]

You never do that?

[Eddie]

Never.

[Brandon Ray]

But I get the point.

[Mike]

Like, anytime I'm playing poker and I try to count my chips or I'm in Vegas, I'm like, don't do it. Kenny Rogers says, don't. There's plenty of time after. Yeah. So I'm thinking, Kenny, I'm thinking I can go Willy again. Almost. Your strategy with on the Road Again, so, Willie.

[Brandon Ray]

On the Road. Yeah, I thought on the Road Again.

[Healthcare Advertisement Voice]

Massive.

[Brandon Ray]

Written for a movie, on a napkin,

[Mike]

on an airplane, in an airplane. From the movie directors. Like, I want to make the movie.

[Kenny]

That's amazing.

[Brandon Ray]

On the Road Again was a massive pop song.

[Mike]

Yeah.

[Brandon Ray]

And that was Dolly's fingernails again. Every rhythm in every country song is Dolly's fingernails.

[Kenny]

Fingernails,

[Mike]

Dolly. I need your fingernails. Those are kind of my two or cruise.

[Brandon Ray]

I mean, I think that's good.

[Kenny]

That's a good pick. No, it is.

[Brandon Ray]

No, it is a good pick. It's a good Pick.

[Mike]

But it would be Cruz. Fgl, right? Or ffgl. Nelly. That's what it is.

[Brandon Ray]

Yeah.

[Mike]

Okay, let's go. Yeah, let's go. Because I went old school with Willie. Old school with Dolly. Middle of the road. Shania Taylor, a little earlier. Let's go. Fgl, Cruise.

[Brandon Ray]

Okay. I think that's a good pick. Is. I almost picked it twice.

[Kenny]

Okay.

[Mike]

I feel good about it.

[Brandon Ray]

So, Mike, whatever the prompt is that you write into AI, would you text it to me so I can put the exact prompt into Claude?

[Eddie]

Yes, I will.

[Brandon Ray]

And when you write it, let me know what it is and say it out loud.

[Mike]

What did we leave on the table?

[Brandon Ray]

On the road again. For sure.

[Mike]

On the road again.

[Kenny]

That's a good.

[Brandon Ray]

I think Shania Twain from this moment on was a massive song that.

[Mike]

Did you really want to take that one?

[Brandon Ray]

Yeah, I thought about it, and the country song was. I think was Brian White. And then she took him off for the pop version.

[Mike]

Oh, really?

[Brandon Ray]

And it was just him.

[T-Mobile Advertisement Voice]

Right.

[Mike]

Trisha Yearwood for the Con Air movie.

[Brandon Ray]

That'd be Leann Rimes.

[Mike]

Oh.

[Kenny]

Oh, it was both of them.

[Brandon Ray]

Yeah, they both sang it. But Leanne Rhymes had the pop one.

[Mike]

Leanne. But so would Leanne Rhymes be blue, too? Blue would have been huge.

[Brandon Ray]

Yeah, probably. Blue would have been big.

[Kenny]

Yeah.

[Brandon Ray]

Okay, so here's the prompt that Mike sent me that I'm gonna put in. Can you rank who has the best team in the debate of best country crossover hits into pop charts? Rank them 3 to 1. Who has the best overall that saw success on pop charts with a position they hit on the pop top 40 and Billboard Hot 100. Okay.

[Mike]

And then you have the whole. All the picks.

[Brandon Ray]

So I'm gonna do Claude.

[Kenny]

I have one that I couldn't figure out.

[Brandon Ray]

Oh, yeah, I gotta take a picture of this. I'll take a picture of the screen and then put the prompt in. What was it?

[Mike]

Right now?

[Kenny]

Act naturally.

[Mike]

The Beatles as a country song.

[Kenny]

Yeah. So Ringo.

[Brandon Ray]

Oh, I was gonna say we do a cover one sometime, but that wouldn't be thrown on a surprise. Like greatest covers of all time.

[Kenny]

That's a good idea.

[Brandon Ray]

So go ahead. I'm sorry.

[Kenny]

It's just Act Naturally from the Beatles. Like, I know that it was. It was one of their biggest songs on all charts.

[Mike]

Okay. I don't even know what we need

[Brandon Ray]

to put into this country charts and pop charts. Or do you think that's just understood?

[Eddie]

I think that's understood.

[Brandon Ray]

Okay.

[Eddie]

I have what I got here. All right.

[Brandon Ray]

I'm gonna hit Come on, baby. I'm gonna hit this send. I took the picture.

[Mike]

I need this.

[Brandon Ray]

I'm not gonna look at it. Hold on. Let me make sure it's going. Thinking.

[Kenny]

I think it's gonna be you, Eddie.

[Brandon Ray]

All right, so I'll read the teams out again before we go here.

[Healthcare Advertisement Voice]

Hold on.

[Brandon Ray]

Claude's still thinking. This is a hard one for Claude. He's struggling with it.

[Mike]

Clyde's like, I can't.

[Kenny]

You got this, Claude.

[Mike]

I can't decide. Right.

[Brandon Ray]

Compiling country crossover, searching the web. Okay, I'll come back to it. Third place, Mike.

[Reese Witherspoon (Advertisement Voice)]

What's this one?

[Eddie]

This is chat GPT.

[Brandon Ray]

What's great is it's going to tell us all the. All the song chart positions.

[Mike]

Got to be kidding me.

[Brandon Ray]

Third place, Eddie mean didn't reach pop top 40.

[Additional Participant]

Wow.

[Healthcare Advertisement Voice]

What?

[Mike]

That was just kind. Oh, okay. Top 40.

[Brandon Ray]

Billboard hot 100.

[Mike]

But billboard one. Okay, 11. All right.

[Brandon Ray]

Willie Nelson didn't reach pop top 40. Billboard hot 100 people. Dolly Parton hit number one. Number one. That was an excellent pick. Nine to five. That's when you got back in the game. We told you like you just now.

[Mike]

I know.

[Brandon Ray]

Fielded a team. Shania Twain, man, I felt like a woman. Number 23.

[T-Mobile Advertisement Voice]

Wow.

[Brandon Ray]

Cruising Nelly. Four on both.

[Kenny]

That's pretty good.

[Brandon Ray]

The strengths for you are nine to five. And Cruz, wow, That's crazy.

[Kenny]

See, you're extra picking there.

[Brandon Ray]

Weaknesses. Mean wasn't really a pop hit. And Willie Julio was more of an adult contemporary than mainstream pop. Okay, so Eddie in third place on this is only one, by the way.

[Kenny]

I feel like after. After seeing this, I feel like I'm gonna be second place.

[Brandon Ray]

So, you know, we should do. We never really came up with the rules for the scoring system. Last time I won because I had two first places. You just want to have the lowest score. So by adding them all together.

[Mike]

Okay.

[Brandon Ray]

Of all three. That's a good point. So you have three points there, Eddie, but you want to have the low. It's like golf.

[Mike]

Got it.

[Podcast Host / Announcer]

At the end.

[Brandon Ray]

You want to have the lowest score.

[Mike]

Got it.

[Brandon Ray]

All right, go ahead. Number two. Oh, crap.

[Environmental Advocate / Advertisement Voice]

Me.

[Podcast Host / Announcer]

Wow.

[Mike]

Look at that, Brandon.

[Kenny]

Wow.

[Brandon Ray]

Bobby's team had the most. Everyone in America knew this song. Energy, Kenny and Dolly. Number one. Number one. Rascal Flats. Bless the broken road. 29.

[Environmental Advocate / Advertisement Voice]

29.

[Kenny]

Wow.

[Brandon Ray]

Johnny Cash. Ring of Fire did not reach pop top 40. Dang.

[Mike]

Look at that, dude. Look at. Amazed.

[Brandon Ray]

Lone star maze. Number one. Rascal flats. Life is a highway. Number 18. Weaknesses. Ring of Fire feels more like an all time classic than a Crossover pop hit. And Bless the Broken Road wasn't huge on pop. Maybe I missed that. I thought it crossed over. Okay, first place, Brandon Faith Hill. Oh, look at all his low numbers. Gosh, Brandon, you dominated one two on Faith Hill. Lady A need you now, number two. Number two, Taylor Swift, Love Story, number one. And number four, Ella Langley, one one.

[Eddie]

Dang. Hey.

[Mike]

And I laughed at you. I said, interesting.

[Brandon Ray]

And Chris Stapleton, 33 and 20.

[Mike]

Look at that. And we both are like, wow.

[Brandon Ray]

Well, that was his weakest one, I think. And that's the one. I think he was the most bullish on Crazy.

[Kenny]

That is wild.

[Mike]

Good job, Brandon.

[Kenny]

Thanks, man.

[Brandon Ray]

So, Brandon one. Me too. Eddie three.

[Kenny]

How did need you now not go number one on country radio?

[Brandon Ray]

This is pop.

[Mike]

No, no. Yeah, the first one's pop top 40.

[Reese Witherspoon (Advertisement Voice)]

Oh.

[Kenny]

Oh, sorry, sorry.

[Brandon Ray]

Yeah, yeah. So these are all country massive hits. We're just now going based on what they were on country.

[Kenny]

Oh, okay. Okay, I see.

[Brandon Ray]

What did they do on pop?

[Kenny]

Gotcha.

[Brandon Ray]

All right, next up. Okay, so Brandon nailed it.

[Kenny]

A.

[Brandon Ray]

Brandy got an A. I got an A minus. And Eddie got a B plus.

[Mike]

And then we all pass.

[Brandon Ray]

I think Chad GPT just doesn't want to be turned off. That's pretty high grade. Yeah. Okay, so let's go over to. And this is going to be Gemini.

[Eddie]

Yeah, Gemini is having an issue.

[Brandon Ray]

Okay, I'll go to Claude.

[Mike]

Gemini still thinking.

[Kenny]

Or Jim.

[Brandon Ray]

Okay, here we go. Let's see. Here's the pop chart draft, graded on actual Hot 100 performance. And there's a twist waiting for you in Brandon's list.

[Mike]

What? That's what it's.

[Brandon Ray]

Why are they doing twist in mine?

[Mike]

All right, let's stop playing games. Let's just do this.

[Brandon Ray]

It says brand. It's not giving me an okay. Here we go. Third place, first, Brandon. Yeah, I think Brandon just gets the first place. It didn't do third place first.

[Kenny]

Oh, man.

[Mike]

So, Brandon.

[Brandon Ray]

So. Hold on. So Brandon, same thing. Faith Hill, Number 2, Taylor Lady A. Number 2, Taylor Swift, 4. Ella Langley, 1. Chris Stapleton, 20. It's basically the same data. We're using data points, so it's the same data. So I finished second, and Eddie's was third.

[Mike]

I suck at this.

[Brandon Ray]

I wonder what the twist is.

[Mike]

Oh, yeah, the fun twist.

[Brandon Ray]

Okay, let's see. Brandon says he's not just winning. Oh, here's the order. Three to one. Eddie solid, a number one in Dolly, but, man, I felt like woman only cracked 35. It's a team with the best floor. But no Real ceiling standout Bobby anchored by an all American all timer with islands in the stream. But bless the broken road, stalling drags it down. Think of it like a fantasy team with one MVP and a bunch of solid role players.

[Eddie]

Rude.

[Brandon Ray]

You suck.

[Eddie]

Gemini, now.

[Brandon Ray]

Okay, Brandon, he's not just winning. He's winning right now. L.L. langley's choosing Texas isn't some old catalog hit. It's parked at number one on the all genre Hot 100 as we speak. Da da da da. Brandon's got the best team and he's still got a song. Climbing while everyone else is playing with history. Okay, Brandon's worst pick is Stapleton. But where's the twist? Is Brandon a woman?

[Mike]

Oh, no. That he's still climbing maybe, man.

[Brandon Ray]

Oh, Brandon's not a ghost. It's always something like, I'm wondering, is Brandon not really here? Is he? AI, Is that the twist?

[Mike]

His name's not Brandon.

[Eddie]

Yes.

[Brandon Ray]

I can't believe I won. Okay, Mike, show me Gemini.

[Eddie]

Hey.

[Mike]

Shocking. Eddie, last, third place, Bobby. Oh, that is shocking.

[Brandon Ray]

Bobby started out strong. Second place, Eddie in first place, Brandon, the winner. He didn't just draft a great country. Shut up.

[Kenny]

No, no, read it. What does this say?

[Brandon Ray]

He has two songs that hit number one pop top 40.

[Mike]

We know. We know.

[Brandon Ray]

He's in.

[Mike]

Yeah.

[Brandon Ray]

Brandon Brand.

[Mike]

They're like, even Tennessee Whiskey was a really good pick.

[Brandon Ray]

Even with Tennessee Whiskey acting as a weaker radio crossover, Brandon's top four are historically unmatched in pop chart performance. So we had to do that last round just to get him to come down to our level.

[Mike]

Yes. Yeah.

[Brandon Ray]

So my total score was 3, 5, 7. Eddie's was 3, 3, 2. Yeah, he was 8. So he finished third place overall. I'm second. Brandon, you're the winner.

[Mike]

Good job, Brandon.

[Kenny]

Thanks, guys.

[Mike]

Proud of you.

[Brandon Ray]

Ella Langley was a good pick.

[Kenny]

Thanks, man.

[Brandon Ray]

And Eddie judge you?

[Mike]

I did.

[Eddie]

He did.

[Kenny]

Oh, interesting. Interesting.

[T-Mobile Representative]

Hey.

[Brandon Ray]

Never heard of her. Good one. That's fine.

[Kenny]

That was really fun.

[Mike]

Great at this game.

[Kenny]

Great.

[Mike]

How do I get better at this game? Like, how can I go home and study?

[Brandon Ray]

You can't, because we don't know what's going to be asked. Otherwise I wouldn't have picked. God bless the broken road. God dang it. So if anybody's ever like, you guys are getting fed these answers. I picked one that didn't even make a chart.

[Mike]

Can I ask one question for we? What would have been the best Taylor song?

[Brandon Ray]

Oh, we can just ask. Ask Chat. Of all of Taylor Swift's crossovers, what

[Mike]

was her biggest yeah, because, like, yours was Love Story.

[Kenny]

Yeah, Love Story.

[Mike]

There was another one, though.

[Kenny]

That was Teardrops on My Guitar. Not that one. It was.

[Mike]

I wear short shirts. You wear a T shirt.

[Kenny]

That one.

[Mike]

What's that called?

[Brandon Ray]

And you belong with Me.

[Mike]

Yeah, you belong.

[Kenny]

That was. That was huge. It's thinking also, like, I feel like with AI, if you took the charts out of it, right? Like, culturally impactful.

[Brandon Ray]

I feel like he's being nice now.

[Kenny]

Look at him.

[Mike]

Like, I think you guys would have won.

[Brandon Ray]

Listen, he knows we're on to him because he's actually AI. So now he's trying to convince us he's not your drafts. You belong with me. Whoever said that, good job. You said that you belong with me.

[Kenny]

Yeah, we're trying to think of it.

[Mike]

Hey, champ. Over here.

[Brandon Ray]

Brandon, GPT Nailed that one, too.

[Kenny]

Taylor Swift.

[Environmental Advocate / Advertisement Voice]

Yeah. Maybe

[Brandon Ray]

we, you know, put in some pram, but we don't know what it's going to be, but. Yeah, I hear you.

[Kenny]

Yeah. Like, I feel like we can talk numbers all day, but, like. Brandon, no, this. This is what I was thinking when we were doing it. It's like, oh, my gosh. Johnny Cash, Ring of Fire. Culturally impactful record sales. You know, you could. You could go off of that, too,

[Mike]

but we're doing crossover, and crossover is mainly these charts, right? Like, that's really what a crossover is.

[Brandon Ray]

I think it was a great exercise in Brandon kicking our butts and.

[Mike]

Dude, take it. You kicked our butts.

[Brandon Ray]

And secondly, Eddie's sucking again. And then every time claims, no, I've won before and never has one.

[Mike]

Are you sure?

[Amazon Health AI / Advertisement Voice]

Never.

[Brandon Ray]

Yeah, there's. I don't. You can't study because we don't know what's going to be.

[Mike]

I just need to get better at this game.

[Brandon Ray]

And you're really intelligent when it comes to music.

[Mike]

Oh, thank you.

[Kenny]

You know what would make it better?

[T-Mobile Representative]

Take.

[Mike]

Here we go. You jerk.

[Brandon Ray]

What?

[Mike]

Brandon. What?

[Kenny]

Take your favorites out of it.

[Mike]

Those aren't all my favorites.

[Brandon Ray]

Pick Julio Iglesias.

[Eddie]

You're right, okay? You're right.

[Brandon Ray]

You work for Halloween. So let's not act like I want this personal bias here.

[Mike]

Every game.

[Kenny]

Every game, you lean toward your favorites. I would do the same.

[Mike]

Oh, shit.

[Brandon Ray]

But he's like someone on the golf course that's giving you swing tips when you never ask for.

[Mike]

I slice the ball all the time.

[Brandon Ray]

Keep your elbow in, man.

[Eddie]

Listen here, sweetheart, all right?

[Kenny]

We've all been there.

[Brandon Ray]

Good job, everybody.

[Mike]

That's fine.

[Brandon Ray]

We'll try again another time soon.

[Eddie]

All right?

[Brandon Ray]

Thank you everybody for watching and we will see you guys next time. Thanks for listening to the Bobbycast. Share this episode with a friend because

[Eddie]

they don't pay to advertise us.

[Mike]

Honestly, Honestly, Honestly.

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[Podcast Host / Announcer]

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[Brandon Ray]

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[Brandon Ray]

Oh, that's actually really simple.

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[Podcast Host / Announcer]

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