We're Here to Help – Episode 201: "The Pickle and Chip Classic & CopperTone Style" (with Beck Bennett)

Date: August 27, 2025
Hosts: Jake Johnson, Gareth Reynolds
Guest: Beck Bennett

Episode Overview

This lively episode features Jake and Gareth bringing their signature irreverence and pseudo-advice, with special guest Beck Bennett (SNL alum, host of "What's Our Podcast?"). The show balances absurd, meandering bits with real listener questions, focusing on two main scenarios: an escalating family pickleball rivalry and a caller nervously preparing to be a live art model at a paint-and-sip event. Packed with quick wit, memorable one-liners, and a genuine effort to help, this episode is a showcase of the hosts' chemistry and ability to turn any conversation into comedy.

Highlights & Headlining Segments

1. Beck Bennett Joins the Show

• [00:38]–[01:52]
  Jake enthusiastically welcomes Beck Bennett, comedically reminiscing over their first meeting at a crab party. Beck plugs his own wild, concept-free podcast with Kyle Mooney ("What's Our Podcast?") and discusses his voice acting in "Fixed," an R-rated dog film by Genndy Tartakovsky.
• Beck’s Show, "What's Our Podcast?" – The premise is that each episode, they don't know what the podcast will be about until a guest pitches one—a concept that leads to hilarious improvisation.
• "Fixed" Movie Chat – They riff about the oddities of R-rated animated movies, with much banter about the tediousness of animating dog buttholes.
  • Quote: "There's just so many buttholes." – Beck Bennett [03:21]

2. Skincare & Sex Appeal Side-Bit

• [05:01]–[07:40] The hosts and Beck spiral into a debate about male skincare routines, chest mics, and "upping sex appeal" through lotions and oils.
  • Beck: “Jesse’s trying to make me. I do lotion. She tries to make me do the lotion with some sunscreen.” [06:31]
  • Gentle ribbing about ‘over-creaming’ and sunscreen paranoia ensues.

Caller 1: "The Pickle and Chip Classic" – Pickleball Family Feud

Starts: [11:32]

Caller: Taylor, Sedona, Arizona

The Situation:

• Taylor is a professional pickleball coach.
• His brother-in-law, Brian (“Ryan”), is mouthy and competitive, insisting he can beat Taylor despite never having played.
• They’re set to see each other in a few weeks, and Taylor wants advice: Crush him and risk family awkwardness? Avoid the match? Or handle it with high comedic flair?

Host & Guest Reactions:

• Beck: Suggests a stealthy surprise match—Taylor preps, then springs the game on his unsuspecting bro-in-law.
  • "He won’t be warmed up... you’re just, you’re going to crush it." [16:13]
• Jake: Advocates for a public, drawn-out trash talk. Let Brian "write checks he can’t cash" in front of the family, putting stakes on the game.
  • "Let him talk his shit... then you go, what are the stakes? Loser has to do what? … a night that’s catered, loser has to be the wait staff." [17:15]
• Family Wrestle Vibes: They compare the scenario to walk-in-challenge guys at boxing gyms and martial arts dojos (“there are levels to this game…” – Jake, [20:50])
• Rewards & Humiliations:
  • Ideas include jackets, shirts, and public announcement of the loser’s defeat.
  • "Taylor dominated me at pickleball because he's more of an alpha dog on the courts." – Jake [21:39]

Live On-Air: They Rope in Brian (Ryan) – The Rivalry Escalates

• [56:41]–[70:26]
• Brian joins the call totally unprepared—immediately trashes Taylor and crows about his own athletic prowess.
• Stakes for the match:
  • Best of three games to 11.
  • Loser must serve dinner to the whole family wearing “elephant trunk speedo” and make a sincere, non-comedic, public humble statement about their defeat.
  • "The other person dominated me at the pickleball court because they are better at that game than me." – Jake [69:15]
• Match scheduled for September 19th in Arizona, with full family audience and video documentation encouraged.
• "The Pickle and Chip Classic" is born—Taylor (“Pickle”) versus Brian (“Chip,” the potato chip delivery guy).
• Both men embrace high-spirited trash talk—Brian: “I got a few chips on my shoulder, so it’s all right.” [67:14]
• "This is the sporting event of the year!" – Jake [65:04]

Key Quotes

• Jake: "This is the We're Here to Help Super Bowl." [65:40]
• Beck: "Bring your squad... signs, hecklers. Whatever you need to do to win!" [66:13]
• Brian: "I look forward to your dad’s facial expression when you serve me a filet mignon in the elephant speedos." [61:14]

Caller 2: Professor T. Squeeze’s Live Model Crisis (“CopperTone Style”)

Starts: [30:01]
Check-in/Update: [73:03]

The Situation:

• Tony (a.k.a. Professor T. Squeeze), calls from Idaho in a goofy, freewheeling style.
• Having (while stoned) agreed to be a live model for a ladies’ paint-and-sip event, he's now panicking and asks for advice on poses, costumes, and how to own the room.

Advice & Banter:

• The guys go wild with ideas: Layered denim “jean-ception” (jeans, then denim shorts, under which more denim, beneath that a banana hammock/leopard print thong), full “CopperTone” pose (beachwear, dog yanking at swimsuit), and slapstick food props (beach towel, beer, sunscreen, hot dogs, spaghetti, honey, ice cream, even bees).
  • Beck: “Maybe a little Winnie the Pooh thing… just shirt covering.” [42:44]
• Tony absolutely runs with the suggestions, determined to be a "legend" in the art class.
  • "You have to be so confident in what you're doing that nobody even questions: was this wrong?... Legends don't ask permission." – Jake [51:29]
• Ultimately, the main pose is the "CopperTone" homage with a banana hammock, plenty of cheek, props, and escalating antics.
  • "Does it ride up the butt a little bit?" – Jake [40:58]
• They recommend hot dogs, beer, and even invite Tony to let audience members remove layers if they're brave enough—"I'm the present these middle-aged women get to unwrap." – Jake [44:38]
• Tony vows to return for a recap and share pics from the event.

Return Visit: Tony’s Follow-Up

• [73:03]–[83:42]
• Tony (now "Dr. Professor T. Squeeze") reports back: He did the full beach-themed, tongue-in-cheek poses, committed to the bit, and shared the photos and art, which the hosts gleefully review.
• "I was swimming in it" – Tony, on being ogled by artists. [81:48]
• Tony is now “Mr. December” for the same art group, promising future updates.

Notable Quotes & Moments

• Beck Bennett, on animators:
  "There’s no version of this [dog butthole] that looks nice." [03:59]
• Brian, on losses:
  "The only one that's going to have an appetite is going to be my wife..." [60:01]
• Jake, on showmanship:
  "This is not the time to go like, can I get permission to be a legend?" [51:27]
• Tony, on his live model debut:
  "Well, I'm not sniffing 50 like you guys, but I'm in my early 40s… but I look like I have reverse Benjamin Button disease." [38:04]

Timestamps of Key Segments

• 00:38 – Beck Bennett's intro and podcast plug
• 03:14 – Animated butthole riff
• 11:32 – Taylor's pickleball dilemma begins
• 16:13 – Hosts debate how Taylor should handle the match
• 56:41 – Brian (the "Chip") called live for pre-match trash talk & stake setting
• 65:04 – The Pickle and Chip Classic is officially set
• 30:01 – Tony/Professor T. Squeeze's call on modeling, bikini-jean shenanigans
• 44:38 – Tony’s “present to be unwrapped” performance concept
• 73:03 – Tony’s follow-up and photo review from his live model gig

Tone & Style

Humorous, good-natured, and riff-heavy, the episode is loaded with playful jabs, extended bits, and a healthy dose of sincere encouragement and engagement with listener dilemmas. The hosts balance mockery with actual attempts to help, always keeping the mood uproarious and never taking themselves too seriously.

Takeaways for Listeners

• Family competition: Sometimes you just need to take the bet, set the stakes, and make a spectacle for everyone’s amusement (but record the conditions!).
• Being a model (or legend): Confidence (and a banana hammock) is key; lean in to the bit and don’t ask permission to be a legend.
• Skincare (and sex appeal): Oil up, wear chest mics, and remember, men love a good two-in-one. (But maybe not all the hype about UV rays.)
• Bro banter: Any listener in need of cathartic, silly, yet honest advice—mixed with endless asides—will find this a defining episode.

Next Steps

• The Pickle and Chip Classic will take place on September 19th—video, photos, and fanfare to follow.
• Professor T. Squeeze will be back for a December modeling recap—who knows what cosplay awaits.
• Listeners are encouraged to send in their stories or advice for future episodes ('Best Advice').

If you haven’t heard this one, you’ll want to tune in just for the escalating family pickleball war and the fully-committed art class legend, Professor T. Squeeze.