Podcast Summary: Wrong Turns with Jameela Jamil – "Trae Crowder and Jessi Klein"

Date: January 15, 2026
Host: Jameela Jamil
Guests: Trae Crowder, Jessi Klein

Episode Overview

This episode of Wrong Turns with Jameela Jamil is a hilarious, self-deprecating celebration of personal disasters and humiliations, featuring comedians Trae Crowder and Jessi Klein. In keeping with the podcast’s premise—reveling in life’s misfortunes with no attempt at extracting silver linings—Jameela and her guests exchange stories of everyday mishaps, celebrity awkwardness, literal wrong turns, and moments where dignity goes to die. The trio commiserate over their embarrassment magnets, with constant wisecracks and mutual support.

Key Discussion Points & Insights

1. Comedic Introduction to Personal Disaster (02:17–03:36)

• The show opens with the concept that the world is falling apart ("we are the Titanic band playing"—Jameela, 02:32), and there's comfort in embracing the dumpster fire with humor.
• Both guests declare disaster a way of life.
  • Trae: “One of my favorite things.” (02:28)
  • Jessi: “This is where we live.” (02:30)

2. Micro-Wrong Turns: Nighttime Sabotage & Cookie Confessions (04:28–06:11)

• Trae Crowder's "literal wrong turn": Trying to be healthy all day, he ends up turning into the kitchen every night for a solitary, shame-fueled binge of Girl Scout cookies.
  • “I stand, eat Girl Scout cookies in the dark, over the sink, alone for 10 minutes.” (05:19)
  • A recurring, relatable pattern of self-abandonment.
• The group bonds over the universality of these nighttime self-sabotages.
  • Jameela: "I don't know if you could name a woman in the 90s who doesn't have exactly the same nighttime routine." (05:56)

3. Cookie Preferences Turn Tribal (06:22–07:16)

• Playful debate over the best Girl Scout cookies.
  • Trae prefers “Lemon Ups” as he ages—"Now I like the Lemon Ups... a little more boring and less in your face." (06:25–06:35)
  • Jessi is team Thin Mints, Jameela dislikes mint-chocolate combos.
  • Jameela: “Do you want to leave?” (06:51)
  • Jessi: “I'm not sure I should stay.” (06:54)

4. Jessi Klein’s Pattern of Accidentally Discouraging Celebrities (07:20–12:34)

• Jessi shares a string of "humiliating micro-encounters" with soon-to-be-famous people:
  • Claire Danes: As a teenager, Jessi discouraged Danes from acting: “Cool, but like, what else?” (08:36). Six months later, Claire was acclaimed as a generational talent.
  • Mark Ronson: At Vassar, Jessi urged him to stay in school instead of pursue music—he did not, and is now wildly successful.
    • "Again, you know, cut to him just really doing pretty great." (10:17)
  • Ethan Hawke: After a kind onstage shoutout at a storytelling show, a future attempted conversation meets "zero recognition."
    • “It was like when a dog is watching the news. Like, no understanding or connection." (11:23)

5. Jameela’s Cringe Encounter with Whitney Cummings (12:34–16:29)

• Nervous and cold after a show, Jameela’s body betrays her:
  • “My entire body decides to go against me and stages a coup against my entire life.” (12:53)
• Whitney responds with compassion, Jameela panics further, then avoids her out of embarrassment for years.
  • “She starts Robin Williams in Good Will Hunting-ing me: ‘It’s not your fault.’” (14:24)

6. Trae & Jameela’s Mutual Celebrity Awkwardness (16:10–19:46)

• Trae Crowder:
  • Tries to relate to Tim Robbins with a half-explained “I was on Bill Maher”—met with utter confusion:
    • “He goes, ‘Okay.’” (18:06)
  • Screams his friend’s name in a room full of A-listers, sticking to the bit out of embarrassment, “Everyone has stopped talking…and finally he was like: ‘What?’” (19:27)
• Jameela: “It’s a version of your brain shitting its own pants.” (18:35)

Major Wrong Turns: Spotlight Stories

7. Jessi’s Epic Driving Debacle (23:55–30:08)

• Context: Grew up in NYC, learned to drive at 33, inexperienced with US traffic law.
• Incident: Mistook police sirens in Griffith Park as pursuing a “perp,” so speeds up and fails to pull over correctly—"I've now led them on like a two mile police chase" (26:55).
  • Pulls over on the wrong side, deeply angers the cop, almost gets arrested for tapping her phone at a light and not updating her license.
  • "Even with the firmest of warnings...I got it changed last year." (29:42)

Discussion:

• Cultural differences in attitudes toward the police; Trae riffs on how rednecks once regarded cops with deep suspicion.
• Jameela shares a story of police failing to respond to a home alarm, so she and her boyfriend arm themselves with a bejeweled baseball bat.
  • “So that if I die defending myself, I die fabulously.” (32:26)

8. Jameela’s English Umbrella Story (32:55–36:15)

• A teacher's purse is stolen from a bathroom stall by someone wielding an umbrella, then thieves pose as department store staff to call and scope out her home, cleaning it out completely.
  • “They'd taken every single thing she owns and even emptied her fridge, which is psychotic.” (34:10)
• Guests joke about the "Britishness" of the umbrella heist and the thoroughness of thieves even stealing expired food.

Main Guest Humiliation Stories

9. Trae’s “Manliness” Humiliation: The Drone Incident (39:15–47:33)

• Admits to having zero stereotypical “redneck” skills; all the house tools belong to his wife.
• At his father-in-law's, he crashes a drone into the top of an enormous tree, immediately after ignoring safety instructions.
  • “As though it had been held captive in a cage and I had just opened the door, this thing shot off towards the horizon.” (41:24)
• Suggests shooting it down, while the 65-year-old father-in-law wordlessly climbs the tree to retrieve it.
  • “He’s climbing the tree like knife in his mouth, fucking cap turned around backwards, calling me a pussy every other branch.” (43:53)
• "I’ll be 80 years old and I’ll wake up to pee at 3am and just be like, ‘You want to try and shoot it?’" (44:17)

Jessi supports Trae: As a mom, she's exasperated whenever her child receives gifts she has to assemble or operate, empathizing with feeling out of depth with technology. (44:50)

Jameela tells a story of a friend who defends his property from paparazzi drones with his own “combat” drones—a “Top Gun dogfight” in her words. (46:42–47:33)

Closing Segment: Misery Loves Company – Wild Wrong Turn Story (47:37–51:16)

• Jameela reads a “Disaster Story” from Florida:
  • 65-year-old millionaire marries a 24-year-old exotic dancer; post-wedding, she discovers she’s married her grandfather.
  • They decide not to divorce, with the bride stating: “Every couple’s different…and I feel our bond is so strong that even something like this is not enough to make us give up.” (50:01)
• The hosts respond with disbelief and gallows humor:
  • Trae: “Pork in your papa should be a deal breaker.” (50:14)
  • Jameela: “It’s an incest sleigh.” (51:10)
  • Jesse: “Florida, man. Come on. Even for Florida.” (50:23, 50:26)

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|--------------|------------------------------------------------------------| | 02:32 | Jameela | “The world is ending and we are the Titanic band playing.” | | 05:19 | Trae | “I stand, eat Girl Scout cookies in the dark, over the sink, alone for 10 minutes.” | | 08:36 | Jessi | “Cool, but like, what else?” (to Claire Danes) | | 14:24 | Jameela | “She starts like Robin Williams in Good Will Hunting: ‘It’s not your fault.’” | | 18:06 | Trae | “He goes, ‘Okay.’” (Tim Robbins, unimpressed) | | 26:55 | Jessi | “I've now led them on like a two mile police chase.” | | 32:26 | Jameela | “So that if I die defending myself, I die fabulously.” | | 41:24 | Trae | “As though it had been held captive in a cage and I had just opened the door, this thing shot off towards the horizon.” | | 43:53 | Trae | “He’s climbing the tree like knife in his mouth, fucking cap turned around backwards, calling me a pussy every other branch.” | | 50:14 | Trae | “Pork in your papa should be a deal breaker.” | | 51:10 | Jameela | “It’s an incest sleigh. Incest sleigh.” |

Important Segment Timestamps

• Welcome and Episode Theme: 02:17–03:36
• Guest Introduction: 03:09–03:31
• Small "Wrong Turns" Stories: 04:28–07:16
• Jessi’s Celebrity Discouragement Pattern: 07:20–12:34
• Celebrity Encounter Disasters: 12:34–19:46
• Jessi’s Big Wrong Turn—Police Chase: 23:55–30:08
• Cultural Attitudes about Police & Burglar Alarm Story: 30:11–36:15
• Trae’s “Manliness” Humiliation (Drone Story): 39:15–47:33
• Misery Loves Company – Florida Disaster Story: 47:37–51:16
• Plugs and Goodbyes: 51:23–52:10

Outro: Where to Find the Guests

• Trae Crowder:

  • Social: @traecrowder
  • Website: treycrowder.com
  • New special: Trash Daddy on YouTube

• Jessi Klein:

  • Instagram: @your acquaintance Jessi Klein
  • Podcast: Here to Make Friends (out Fridays, about adult friendship)

Summary Tone

The tone is dry, wry, and relentlessly self-mocking. No story is too small or too dark to laugh about; embarrassment and failure are a shared human sport. As Jameela sums up, “We’re a community of clusterfuckers.” The episode is a perfect example of comedy as catharsis, with each guest's anecdote more ridiculous (and relatable) than the last.