B&T Extra: Comedian Derrick Stroup

Summary

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The BOB & TOM Show Free Podcast

B&T Extra: Comedian Derrick Stroup

Date: September 4, 2025
Guest: Derrick Stroup

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Episode Overview

This B&T Extra episode sees the BOB & TOM crew welcome stand-up comedian Derrick Stroup for a fast-paced, comedic conversation. The main theme centers on airport and airline mishaps, with plenty of jokes, playful ribbing, and a deep dive into the quirks of the Denver airport and the world of airline seating. The hosts and Derrick riff on travel woes, the peculiarities of modern conveniences like digital tickets, and Southwest Airlines' unique boarding system—all with their hallmark wit.

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Key Discussion Points & Insights

1. Denver Nuggets Hat and Team Misidentification

[03:05–04:35]

• The crew quizzes Derrick on the sports team hat Tom is wearing, which sparks banter about team logos and states.

• Notable Moment: Derrick humorously guesses "The Confederacy" after failing to identify the Denver Nuggets logo at a distance, leading to playful teasing around historical (and hysterical) misunderstandings.

  • Quote:
    "I believe that's 1862. That's the Confederacy." — Derek Stroup (03:30)

• Baseball bats, pickaxes, and skiing all get thrown into the mix before Bob reveals it’s the Denver Nuggets, further highlighting how the logo can be confusing.

2. Denver Airport Woes and Travel Stories

[05:03–10:36]

• Tom and Derrick bond over shared experiences with Denver and its infamous airport, including high Uber costs, constant construction, and inconvenient distance from the actual city.

  • Quote:
    "There's no way I'm taking a $75 Uber to take an $85 United flight." — Tom (05:23)

• Tom affectionately refers to Denver as the "connection city," noting its convenience for direct flights, but bemoans the never-ending construction and logistical headaches surrounding travel there.

• Derrick launches into a story about almost missing his flight due to confusing construction layout, unclear gate changes, and a lack of announcements or text updates from the airline.

  • Quote:
    "If you've ever been to the Denver airport, when you look at TSA, it's like looking at a photograph of Ellis Island, but there are more people there." — Derek Stroup (09:45)

3. Airline Boarding Mishaps, Digital Tickets, and Southwest's System

[10:36–14:23]

• The group debates airline boarding procedures, with Derrick expressing a preference for paper ("hard") tickets because technology "scares" him, getting laughed at for being "old-fashioned."

  • Quote:
    "That phone thing really scares me." — Derek Stroup (12:07)

• The conversation shifts to Southwest's unique open seating, inspiring Tom to vent about the stress and confusion of boarding order, and his dislike of passengers who downplay the importance of assigned slots.

  • Quote:
    "You don't feel that way when you're in middle seat in row 42!" — Tom (14:00)

• Discussion of people playing Candy Crush instead of showing their boarding position, with Tom recalling a time he defended his wife from being pushed back in line, highlighting social awkwardness and the need for airline etiquette.

  • Quote:
    "I took her ticket, and I went through the line... 'A30? Head on back, big dog!'" — Tom (14:50)

• The crew jokes about comedians faking an injury to get into pre-boarding (15:23), ribbing each other about travel hacks and “heroes” of airline seating charts.

4. Conspiracy Theories and Legends about Denver International Airport

[09:57–10:36]

• Tom brings up the popular conspiracy theories about Denver Airport—including rumors about underground buildings, signs referencing aliens, and the infamous blue Mustang sculpture known as "Blucifer."
  • Quote:
    "There's, like, a lot of conspiracy theories with that airport... They lean into it." — Tom (09:57)
  • The hosts laugh about how DIA’s marketing cheekily references these rumors in construction delay signage.

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Notable Quotes & Memorable Moments

• On confusing airport info:
  "I was literally sitting there for two hours, and I finally look up. I go, what is this thing in a board? So I walk up to the guy and I go, when is this flight boarding? Because, oh, we changed the gate. Said, well, maybe an announcement would have been nice." — Derek Stroup (08:13)

• On digital tickets:
  "That phone thing really scares me. Yeah. I hate to break it to you." — Tom (12:07)

• On Southwest’s boarding culture:
  "We're all trying to—he would not just share your position, because I'm somebody, you know... It doesn't matter, we're all going to the same place. And I go, you're a psychopath, man. You don't feel that way when you're in middle seat in row 42!" — Tom (13:36)

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Timestamps for Key Segments

• 03:05 — Denver Nuggets Hat Misidentification/Banter
• 05:03 — Denver Travel, Airport Complaints
• 08:13 — Gate Change and Comedy of Travel Errors
• 09:57 — Denver Airport Conspiracy Theories
• 10:36 — Hard vs. Digital Tickets and Tech Anxiety
• 12:07 — Old-Fashioned Travel Habits
• 13:30 — The Madness of Southwest Open Seating
• 14:50 — Tom Defends His Wife’s Boarding Place
• 15:23 — Pre-Boarding Faker Anecdote

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Episode Tone and Style

The show maintains its quick-witted, light-hearted, and improvisational style throughout. Most of the humor stems from the crew’s personal gripes and light self-deprecation, punctuated by Derrick’s earnest, slightly bewildered traveler persona. The banter is affectionate but sharp, making the everyday frustrations of travel the heart of the comedy.

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Summary for the Uninitiated

If you’ve ever been confused by an airport, annoyed by airline boarding chaos, or bewildered by “that phone thing,” this episode is for you. Derrick Stroup’s relatable tales of travel folly, paired with the BOB & TOM crew’s relentless joking and clever asides, turn ordinary pains into comedic gold. The episode delivers quick-fire jokes, relatable anecdotes, and a tongue-in-cheek look at the madness modern air travel can bring.

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Transcript

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[Christopher]

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[Derek Stroop]

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[Christopher (Outro)]

Welcome back. It's another Bob and Tom ext. This is Christopher. Not only is the Bob and Tom show live every weekday morning, but every afternoon we'll give you a little extra. In case you missed anything on the big show today, comedian Derek Stroop. He's coming up in just a minute.

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[Bob]

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[Derek Stroop]

Uh huh.

[Bob]

Have a Slim Jim Fast for breakfast, another Slim Jim Fast for lunch, and top off your day with a sensible convenience store dinner. Say a hot dog, burritos, donuts. Hell, have another Slim Jim Fast for a bedtime snack. I'll get that balloon dart game job on the midway for sure. Now looking all drifter like Slim Jim fast.

[Tom]

All right, step right up. Hey, how about you, sport break three.

[Bob]

Balloons and win a Dick Trickle mirror and a pack of smokes for the little lady? Oh, yeah.

[Derek Stroop]

Oh, yeah.

[Tom]

It's our way of making sure you haven't missed anything.

[Bob]

This is Bob and Tom. Extra.

[Derek Stroop]

We're joined by a very handsome guest.

[Bob]

And we're going to play a game, and it's including Tom, and you're going to be excited. Go ahead, say hello.

[Derek Stroop]

Our guest is comedian Derek Stroop. Hey.

[Tom]

Hey, how y' all doing? Thanks for having me.

[Derek Stroop]

The big D. It's a pleasure.

[Tom]

Come on, Derek. Derek.

[Bob]

Now, hang on before you ask a question.

[Derek Stroop]

Okay, sure.

[Bob]

What hat is he wearing? Can you. Can you tell what team, what league? For extra credit, I'm going to say what year?

[Derek Stroop]

I believe that's 1862. That's the Confederacy.

[Christopher]

Oh, Jesus.

[Tom]

That'll go well with my accent. Real, real zinger out the gate here.

[Derek Stroop]

I can't he see it from here. What is it? Are those baseball bats?

[Bob]

I'll tell you, it's the NBA.

[Christopher]

Yeah. It's a basketball team.

[Bob]

You can see the. There's a basketball at the bottom.

[Derek Stroop]

I can't see.

[Josh]

A couple pickaxes.

[Bob]

A couple of pickaxes.

[Christopher]

And.

[Bob]

And it's. It's. A lot of skiing goes on in this state.

[Derek Stroop]

So it's not the Globetrotters?

[Tom]

No.

[Josh]

What does that even mean?

[Christopher]

I don't know.

[Derek Stroop]

Well, I mean, how many of the Globetrotters ski? Come on.

[Tom]

Oh.

[Josh]

You know, I wouldn't know. I'm not too sure.

[Bob]

Are you sure you don't know?

[Josh]

I know they're not allowed to ski where you ski.

[Bob]

That's right. It's the 2022. 2023 world champion. Denver. Denver.

[Derek Stroop]

That's the Timberwolves.

[Bob]

It's the Denver Nuggets.

[Derek Stroop]

Look at their axes on there.

[Josh]

They're pickaxe.

[Tom]

They're the Denver Nuggets of cold.

[Derek Stroop]

See, it looks like a big X where I'm sitting. It's.

[Tom]

Yeah, yeah.

[Derek Stroop]

Derek's 30ft away from me.

[Bob]

Yeah, but it's a logo, and you can see what it is. Josh is the same distance. And he said they're pickaxing.

[Josh]

Yes.

[Bob]

You jerk. That's all right, Derek. So I want to be here.

[Derek Stroop]

I was at a freebie. Or are you a fan?

[Tom]

No, I'm a fan. Yeah. I lived out there for almost 11 years.

[Bob]

In Denver?

[Tom]

Yeah.

[Derek Stroop]

Ah, yeah, I was just there.

[Tom]

Yeah. Yeah. Okay. You were just in Denver?

[Derek Stroop]

I was at the airport.

[Tom]

Oh.

[Bob]

Oh, well, same thing. Yeah.

[Josh]

But he was in Colorado.

[Tom]

Well, I can tell you, if you were at the Denver airport, you weren't in Denver.

[Josh]

That's for sure.

[Tom]

You were closer to touching Kansas.

[Derek Stroop]

Yeah, I've said that for years. When they built that new airport, they said. Someone said, I got on a deal. Let's go farther away.

[Tom]

Ye. There's no way you can tell me that Uber didn't have a hand in that airport. There's no way I'm taking a 75 Uber to take an 85 United flight. There's no way. There's no way Uber didn't go. Now put it out there a little bit.

[Derek Stroop]

Oh my God.

[Bob]

I never thought of that.

[Christopher]

Yeah.

[Bob]

Where we live, our Ubers are 75, 80 bucks. And they have fair wars every now and then.

[Derek Stroop]

Gee, many Chris, that airport is perpetually being constructed.

[Tom]

It is, it is.

[Derek Stroop]

I don't. I mean, I remember.

[Tom]

I mean. Now, here's the thing about flying out of Denver. You got a direct flight. I mean, to villages. I mean, you can fly anywhere because it is. It is the connection city. I miss that. I live in New York City now. But flying out of Denver has got to be one of the best cities. I mean, some of your flights might be a little longer, yada, yada, but it's directs everywhere.

[Bob]

You're right.

[Derek Stroop]

It's a nice hub.

[Tom]

Yeah, yeah, it is. It is.

[Derek Stroop]

I was the last one on my plane. It's a long story. I won't bore you with. Let's talk about Derek. But you have some game involved.

[Christopher]

Wait a minute.

[Bob]

Identifying the hat. Because you were going to say what type of hat is that you're wearing? Or something like that.

[Derek Stroop]

No, I was going to say who are you named after?

[Tom]

Who? What are you talking about? My first name. Derek.

[Derek Stroop]

Derek.

[Tom]

I don't think I'm named. I mean, I'm not named after anybody.

[Bob]

His dad. No, no. His dad fought oil well fire.

[Tom]

Yeah, I beat him to it.

[Bob]

Yeah.

[Derek Stroop]

Yeah. The correct answer would have been Eric Clapton, Derek and the Dominoes. But we'll move on.

[Tom]

Yeah, yeah, yeah, yeah.

[Bob]

Eric's doing well for himself.

[Josh]

Yeah, it's even spelled differently.

[Christopher]

So you were the last one on your plane. Were you traveling alone?

[Derek Stroop]

Yes.

[Josh]

You're being the last one on your plane is not the last one.

[Tom]

You were at the wrong gate.

[Bob]

No, no, no, I got it. Were you asleep?

[Derek Stroop]

No, no, I got there two hours early.

[Christopher]

Yeah.

[Derek Stroop]

And my gate was. There was a construction thing there, so it was kind of half cordoned off.

[Bob]

Your family's got it down. Traveling with you don't.

[Derek Stroop]

They.

[Bob]

They. Which is the best way to travel.

[Derek Stroop]

Yeah, they went separately.

[Bob]

Yeah.

[Derek Stroop]

Yeah. And there was. And I, you know, got there early, looked at the big screen, got one.

[Bob]

To my gate, and I can't imagine him going around.

[Derek Stroop]

They had the desk there with the sign saying where it's going.

[Christopher]

You didn't even talk about your TSA adventure. You couldn't find the pre check and.

[Derek Stroop]

Well, but it was great. And everyone was super friendly in tsa, both here and there.

[Christopher]

Thank you.

[Bob]

Well, you didn't have to go through Philadelphia.

[Tom]

Why were you the last person on your flight?

[Derek Stroop]

So I positioned myself right near the door to the jetway. Yeah. Because I want to be the. You know, I want to get the plane. Oh, sure. Because I had a nice, nice ticket, and so I.

[Tom]

Nice.

[Bob]

Hey, hey. Josh is your first class. When Tom flies, he has a nice ticket. Oh, yeah, yeah, yeah.

[Josh]

It's made out of satin.

[Bob]

Real nice.

[Derek Stroop]

It's kind of hard to explain because.

[Bob]

Bastard.

[Derek Stroop]

There's, like, police tape everywhere. They're. They're building something, and so I. I.

[Bob]

Wait a minute. What airport is this?

[Derek Stroop]

Denver. Okay. So I finally. I'm literally sitting there for two hours, and I finally look up. I go, what is this thing in a board? So I walk up to the guy and I go, when is this flight boarding? Because, oh, we changed the gate. Said, well, maybe an announcement would have been nice.

[Josh]

I guarantee they made.

[Bob]

No less than 7.

[Derek Stroop]

I was right there because they'd had. They'd move the normal desk. The desk for that gate.

[Christopher]

Right.

[Derek Stroop]

Is not working. So they were down at the next one.

[Christopher]

Yeah.

[Derek Stroop]

So if they made an announcement, I didn't hear it because I was too close to the actual.

[Christopher]

Did they not send you a text? They always text you.

[Derek Stroop]

That's what I want to.

[Tom]

They see your nice, nice ticket.

[Bob]

Yeah. What about your nice ticket?

[Derek Stroop]

I had a very nice ticket.

[Christopher]

I always got. I get.

[Derek Stroop]

I know. That's. That was what Kelly and I were talking about last night. Why didn't they text everybody? They changed the gate. The guy goes, well, we changed it on the big board. Well, that's great. So I have to get up and walk halfway down the airport to find the big board.

[Josh]

I think being blast on the plane is a gift.

[Christopher]

It is a gift. It really is.

[Josh]

No, you love sitting there while everybody else boards.

[Derek Stroop]

No, worse. It was.

[Bob]

Yeah, but everybody else can't see him in his nice ticket seat.

[Christopher]

It was a nice, nice ticket. So he got a free drink.

[Derek Stroop]

No, no, no.

[Tom]

It was.

[Derek Stroop]

I. It was one of those choose your own seat seats.

[Bob]

So that is terrible. I got.

[Derek Stroop]

I got wedged between two people.

[Christopher]

Okay.

[Derek Stroop]

And then my carry.

[Josh]

A nice ticket at all.

[Derek Stroop]

My carry on had to be sent to the back of the plane. So when it landed, I had to.

[Tom]

You had a middle seat. Oh, my goodness.

[Derek Stroop]

It was nice. They were nice. It was fun. But in any event, that's that airport. When are they ever going to finish it? If you. If you've ever been to the Denver airport, when you look at tsa, it's like looking at a photograph of Ellis island, but there are more people there.

[Tom]

Yeah. Yeah. And also, I mean, they really lean in. There's a lot of conspiracy theories with that airport about that. There's, like, this underground kind of thing going on. They lean into it.

[Josh]

They're, like, literally underground.

[Tom]

Yeah, there's. There's all kinds of conspiracy theories about the DIA There. There has been for a while. You know, they got Lucifer, the. That bronco. That blue bronco, red eyes and fell on the guy that. That sculpted it and killed him. And so that's, like that. That's, you know, one of the stories around there. But, yeah, they lean into it. They're like, sorry for the delay on construction. We've been trying to. We've been dealing with aliens. Like, they have signs that really lean in, lean into it.

[Derek Stroop]

But, yeah, interesting. Interesting. But, yeah, it was great. Great place. Love my pilots. Lovely everyone working on the airlines. They're great.

[Christopher]

Glad you didn't miss your flight.

[Derek Stroop]

It was. They shut the door to the jetway.

[Christopher]

Oh. Usually they won't reopen it.

[Derek Stroop]

Not. Not. Not the plane. The. The end of the jetway. Where it ends in the airport.

[Christopher]

Yes.

[Derek Stroop]

And I said they didn't change the location on the board where I was sitting because I'd gotten there two hours early. So I've learned a lesson, which is every 10 minutes, walk up there and say, is this still the gate?

[Josh]

Oh, no, that's not the lesson.

[Tom]

The screen.

[Derek Stroop]

Check your text.

[Bob]

No, no, I did not get a text.

[Derek Stroop]

I. I'll show you my phone. No text.

[Bob]

Is it possible. I'm. I'm. I'm really trying to make some progress with you today. Is it possible that any of this was your fault?

[Derek Stroop]

No, I've got. I had a hard ticket, and it says the gate right there.

[Bob]

And they.

[Derek Stroop]

Gate 40. You.

[Bob]

They. There's no way they could have made an announcement and you missed it.

[Christopher]

What gate did it go out of?

[Derek Stroop]

Like, why.

[Tom]

Why did you have a hard day?

[Christopher]

Wait, 40 and you. What gate did it go out of 50?

[Derek Stroop]

51.

[Christopher]

Oh.

[Derek Stroop]

Oh. So I got some extra steps in.

[Christopher]

Yeah, you did. Fast.

[Derek Stroop]

Yeah, running. It was close.

[Christopher]

Anyway, he has a hard ticket because he's, he prints them at the.

[Derek Stroop]

No, because I was checking a bag and when you check a bag for. I guess they automatically gave me a ticket. Oh, I don't know. But that phone thing is, that scares me. I like having a hard ticket where you put your ticket on the phone.

[Tom]

I love. That's a tough sentence in 2025. That phone thing really scares me. Yeah. I hate to break it to you.

[Bob]

But there's no, there's no wires. You still always get a hard ticket.

[Derek Stroop]

I did in this. I didn't. Not always, but I did in this case and it was.

[Josh]

Well, that phone thing really scares me. Could have been A quote from 1907.

[Bob]

100.

[Tom]

Yeah. And he goes, have y' all heard about debit car? Are you kidding me? My bank's on a card.

[Christopher]

It could be on your phone.

[Derek Stroop]

I know, but I know Kelly had. What is it called? She had texted me the ticket the day before. I looked at it, went, that's great. And when I got to the airport, it wouldn't open up. Oh. So I had to do some homework. I called Killen. I said, hey, can you resend me the ticket? It won't open up.

[Tom]

And she said, what?

[Derek Stroop]

Oh, I'm sure she was.

[Bob]

At any point during that conversation, did you hear like a mute button go on or anything on her end or.

[Derek Stroop]

I like a hard ticket.

[Tom]

I want to be able to, I.

[Derek Stroop]

Want to be able to prove I deserve to be on this plane.

[Bob]

Oh, they, they know.

[Tom]

Probably.

[Derek Stroop]

Yeah. And they're doing an ad campaign at Southwest. Assigned seats, right? Do people like assigned seats?

[Christopher]

No, I, they, I think people like the way Southwest does it.

[Derek Stroop]

I do.

[Christopher]

Yeah.

[Derek Stroop]

Great.

[Christopher]

Especially unless you miss your A group.

[Bob]

I'm sorry. I like the way first class works.

[Josh]

Is how I like it.

[Christopher]

Yeah. If you can afford that.

[Derek Stroop]

They don't have first class class.

[Tom]

Well, here's my thing with Southwest. I, I, I like the open seating once I'm on the plane. I hate the pre boarding process where everybody's kind not showing their cards and kind of you. I've got to go. I got to go shake people down to see if they're really a 31. You should have your phone. I, I can't. This guy yesterday would not move. He had Candy Crush out. I mean in man in his 50s just going for a high score. We're all trying to. He Would not just share your position because I'm somebody, you know, you'll hear somebody go, it doesn't matter. We're all going to the same place. And I go, you're a psychopath, man. You don't feel that way when you're in middle seat in row 42. I'll go, no, we're all headed to Orlando.

[Derek Stroop]

Yeah.

[Bob]

That's crazy.

[Tom]

Yeah. I want everybody in their right position.

[Bob]

Yes.

[Tom]

Yeah.

[Christopher]

Yeah. You paid extra for that? You want it?

[Tom]

Yeah.

[Josh]

Give you cards you have to tape to your forehead.

[Tom]

I feel that way. I really do. One time, me and my wife, we were flying at a separate gate, same airport in Pennsylvan, Pensacola. I was flying United, she was flying southwest. She's very. She's very introverted, young lady. Okay. I saw her just getting pushed to the back, to the back. I went over there, I took her ticket, and I went through the line. I went, hey, are you a. Oh, a 30. Head on back, big dog. I took Alyssa all the way to the front of the line. Everybody was looking at me like, oh, he's a psycho. But Alyssa was standing exactly where she should because they were bullying her. I mean, they were pushing her back because she's not going to fight her way and force her phone in their face. So, I mean, I had to go over there, and it was. It was awkward, I'm not gonna lie. But she was good. You know, I'm just that type of guy.

[Derek Stroop]

I've actually seen them do a thing where someone comes up and they go to scan the ticket. No, no, no, no, no, no. You're not in the A group.

[Christopher]

Yes, I've. I've seen that.

[Tom]

Real hero. Yeah, I.

[Bob]

An American hero.

[Derek Stroop]

The Lindbergh of seating charts.

[Tom]

I travel with a comedian who faked an injury to get on the.

[Derek Stroop]

The first group. Really?

[Christopher]

Yep.

[Josh]

We got good seats, though, didn't we, Pat?

[Christopher (Outro)]

That's it for another Bob and Tom show. Extra. Catch us on itunes, Google Play and Stitcher for Bob and Tom. Extra. This is Christopher. Take care, everybody.

[Tom]

Football season is here.

[Bob]

Oh, man.

[Tom]

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[Bob]

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[Tom]

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[Bob]

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[Tom]

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[Josh]

That's B L E A V podcast.

[Tom]

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