Bad Friends – "Dead Dad's" w/ Harland Williams

Hosts: Bobby Lee & Andrew Santino
Guest: Harland Williams
Date: September 1, 2025

Episode Overview

This episode of Bad Friends features comedian Harland Williams joining Bobby Lee and Andrew Santino. The trio embarks on their signature blend of freewheeling, absurdist banter, personal confessions, and playful roasts. The core theme revolves around vulnerability between friends, dealing with loss (especially the passing of fathers), the odd rituals and traditions that come with grief, and the comedic ways people mask discomfort and emotional distance. Alongside these sincere undercurrents, the episode is packed with running gags, surreal storytelling, and the group’s irrepressible shame-free humor.

Key Discussion Points & Insights

1. Aging, Botox, and Asian Stereotypes

[00:27–02:27]

• Bobby jokes about getting Botox after seeing an unflattering photo (“Do I look like a shrinking frog?”).
• Harland encourages accepting aging, referencing Asian stereotypes about "waking up as Yoda" overnight.
  • Quote:
    “One night long ago…I went to sheep. I woke up as Yoda.”
    – Bobby Lee [01:59]
• Light-hearted banter about wisdom, knowledge quizzes, and aging gracefully.

2. City & Music Trivia Game

[02:27–05:19]

• Harland quizzes Bobby on geography and album trivia, leading to amusing mistakes and correct answers.
• The segment highlights Bobby’s self-deprecating humor and the group's camaraderie.
  • Quote:
    “Albany, New Mexico…No, Albany, New York. That was a tough one.”
    – Bobby Lee [02:57]
  • Quote:
    “You know a lot of stuff, dude.”
    – Harland Williams [04:49]

3. Fun Tang, Dating & Physical Comedy

[06:28–08:41]

• The hosts riff on the meaning of “Fun Tang,” using it as innuendo for action (“When’s the last time you had Fun Tang?”).
• Discussion about one-night stands vs relationships in Los Angeles.
• Hilarious detour into Bobby and Carlos’s kissing techniques.
  • Quote:
    “What I do is I don’t go tongue first. I don’t do bonsai style…I don’t do sneak attacks.”
    – Bobby Lee [08:05]
  • Group riff comparing Pearl Harbor to kiss sneak attacks, featuring Bobby: “I back off. I don’t actually hit Pearl Harbor.” [08:24]

4. Titanic, Noah’s Ark & Cultural Commentary

[10:18–13:30]

• Imagining alternate historical scenarios (e.g., a kamikaze who becomes king of a Hawaiian island).
• Joking about the diversity of passengers on the Titanic and overlooked history.
  • Quote:
    “They don’t want to admit the truth, that they want you to still go to the museum. That’s why.”
    – Harland Williams [11:09]
• Musical interlude: The group sings and analyzes the “Noah’s Ark” song, poking fun at omitted animals.
  • Quote:
    “But you won’t see no dinosaur—that is the real song.”
    – Harland Williams [12:26]

5. Sadness, Performance Anxiety & Vulnerability

[13:44–15:12]

• Bobby opens up about recent struggles:
  “The last two weeks have been the worst two weeks of my life.”
  – Bobby Lee [13:44]
• Harland and Andrew reassure Bobby, noting his strong performance at The Comedy Store.
  • Quote:
    “You seem to notice that 10 out of 10, though…you didn’t miss.”
    – Harland Williams [14:00]

6. Burning Man, Making Art, and Fear of Releasing Work

[20:09–22:48]

• Andrew shares stories about Burning Man: its barter system, transformative power, and the beauty of the experience.
  • Quote:
    “Everyone in the world should go…If you need something, you knock on a trailer. ‘Give me a sandwich.’”
    – Andrew Santino [21:11]
• Andrew admits to having made but never released a documentary (“Burning Men”) and discusses creative insecurity.
  • Quote:
    “It’s all done, edited, everything…But I do a lot of that. I’ll make things and never put them out.”
    – Andrew Santino [22:28]

7. Leg Strength, Secret Athleticism, and Competitive Drive

[23:11–24:11]

• The hosts share anecdotes about their unexpected athletic prowess.
• Discussion shifts to racquetball games with Dane Cook (“He’s new, I’ve been playing for, like, nine years…” – Santino [24:04]).

8. Absurd Therapy, Ouija Board Bit & Emotional Honesty

[25:02–27:46]

• Harland invents a “Ouija Therapy” class at DeVry, assigning facial expressions to letters.
• Surreal bit about communication as Ouija séances.
  • Quote:
    “Because your face is so expressive…they sort of assign areas of your face, almost like the keypad.”
    – Harland Williams [25:19]

9. Books, Anxiety, and the Special’s Pressure

[28:01–31:27]

• Sharing book recommendations: Ayn Rand’s The Fountainhead, Stephen King’s The Stand, and Bobby’s choice Hear Yourself.
• Bobby discusses meditation and tackling anxiety about his upcoming special.
  • Quote:
    “Nothing. I don’t know what it is, but I’m trying to…a lot of anxiety. So I’m trying to calm…”
    – Bobby Lee [31:06]

10. A “Chocolate” Guru & Master-Disciple Skit

[31:48–34:33]

• Andrew becomes a satirical “chocolate master,” doling out advice with faux profundity.
• The segment lampoons spiritual advice and dodges real solutions with humor.
  • Quote:
    “Chocolate.”
    – Andrew Santino, deadpan as “master” [32:17]
  • Quote:
    “Ride the anxiety like a snake, like a dragon…just take it onto the stage.”
    – Andrew Santino [34:33]

11. Imposter Syndrome & Handling Fame

[34:03–35:52]

• Bobby reflects on imposter syndrome and the challenge of public recognition.
  • Quote:
    “I just have a conflict about it. What do I do, Master?”
    – Bobby Lee [34:16]

12. Gross-out & Cultural Rituals: Shoeys and Spa Nudity

[47:50–48:46], [65:56–66:43]

• Harland demonstrates an “Australian shoey” (drinking out of your shoe) for laughs.
  • “You pour a drink in it and you chug it.”
    – Harland Williams [49:02]
• Later, they discuss emotional barriers and consider spa nudity as a possible solution to connect more deeply.
  • “We should go to the Wii Spa…sit around like real men and just real men.”
    – Harland Williams [65:59]
• Ridiculous but surprisingly honest talk about embracing vulnerability among male friends.

13. The “Dead Dad” Story & The Corn Shirt

[42:44–46:58]

• Santino tells a deliberately absurd story about his father’s comically outrageous “final destination”-style death involving a marlin, a ceiling fan, and piranhas, all while wearing a corn-print shirt.
  • Quote:
    “We’re sitting there, Malachi pops out…The old man goes back, hits the wall…The marlin cuts loose from its hanging…The snout goes into the old man’s spine…He put his hand into the piranha tank, these things took off two of his fingers…”
    – Andrew Santino [44:25]
• The group roasts the shirt and riffs on grief traditions, using surreal storytelling to process genuine emotions.

14. Barriers, Vulnerability, and Male Friendship

[56:00–64:15]

• The trio get “real” about opening up, emotional walls, and feeling distant or misunderstood despite years of friendship.
  • Quote:
    “Buddy tries to get in, and you guys will open the door so far. But then Buddy…can’t get all the way in and be Buddy. Buddy.”
    – Andrew Santino [58:17]
  • Quote:
    “The janitor built a wall. And I need you to get over that wall…and come to me.”
    – Andrew Santino [62:32]
• In a rare serious burst, Bobby expresses affection and trust for Andrew, and the trio agree there’s a childlike glee in their dynamic—while still poking fun at their inability to truly open up.

15. Riddles, Puzzles, and Classic TV

[69:45–73:14]

• Bobby and Andrew trade classic riddles, including the “female surgeon” puzzle from All in the Family.
  • Quote:
    “That riddle came from an episode of All in the Family…In the ’70s, that was actually a very difficult riddle…”
    – Andrew Santino [71:04]
• The trio end the show in playful, sharp-witted competition.

Notable Quotes & Memorable Moments

• “Do I look like a shrinking frog?”—Bobby Lee commenting on aging [00:46]
• “I’m gonna turn into Yoda one day.” — Bobby Lee [02:10]
• “It’s a mechanical error. I couldn’t do it. Then you swim to Hawaii and go, I’m Hawaiian.” — Bobby Lee (on dodging a kamikaze mission) [09:00]
• “Nothing says a good sandwich in the desert like tuna.” — Harland Williams [21:46]
• “You know a lot of stuff, dude.” — Harland Williams [04:49]
• “I’ll make things and never put them out…I think we all do that as artists.” — Andrew Santino [22:28]
• “Chocolate.” — Andrew Santino as the guru [32:17]
• “Ride the anxiety like a snake, like a dragon…just take it onto the stage.” — Andrew Santino [34:33]
• “We’re just two kids in a schoolyard, jumping with glee.” — Bobby Lee [62:11]
• “The janitor built a wall. And I need you to get over that wall.” — Andrew Santino [62:32]
• “We’re a Nancy Drew, Hardy Boys mystery type of setup where maybe we don’t want to give the ending away.” — Andrew Santino [69:16]
• “[On dad’s death:] My old man, it’s like a Final Destination…” — Andrew Santino [45:31]
• “Drink out of your shoe! That’s what Australians do.” — Harland Williams [48:49]

Timestamps for Key Segments

• Botox, aging & Yoda joke: [00:27–02:27]
• Trivia game & knowledge talk: [02:27–05:19]
• Fun Tang & kissing styles: [06:28–08:41]
• Titanic & Noah's Ark songs: [10:18–13:30]
• Bobby opens up about sadness: [13:44–15:12]
• Burning Man doc & insecurity: [20:09–22:48]
• Comedy, books & anxiety: [28:01–31:27]
• Chocolate master guru skit: [31:48–34:33]
• Imposter syndrome/fame: [34:03–35:52]
• Father’s bizarre death (corn shirt): [42:44–46:58]
• Shoeys and spa nudity to promote vulnerability: [47:50–48:46] / [65:56–66:43]
• Getting “real” about friendship: [56:00–64:15]
• Riddles and classic TV reference: [69:45–73:14]

Summary & Takeaway

Dead Dad’s w/ Harland Williams covers a colorful, unfiltered, and surprisingly touching journey through male friendship, grief, emotional evasion, and the struggle to form meaningful connections. While the show remains grounded in offbeat, rapid-fire comedy, it exposes the anxiety, imposter syndrome, and yearning for intimacy beneath the surface. Whether they’re roasting each other over corn shirts, recounting surreal death stories, or negotiating the boundaries of vulnerability, the trio reveals how comedy can both shield and reveal genuine feeling. It’s a classic Bad Friends episode: wild, weird, but ultimately quite human.