Club Random with Bill Maher

Episode: Cheryl Hines | Club Random
Date: November 10, 2025

Episode Overview

This episode features actress and author Cheryl Hines (Curb Your Enthusiasm, Unscripted) joining Bill Maher for an open, fun, and sometimes intimate conversation about marriage, political culture, social media, showbiz hypocrisy, health, personal growth, and more. True to Club Random’s format, Maher and Hines keep it freewheeling and candid—exploring everything from the pressure of living in the spotlight to political tribalism, relationship dynamics, cancel culture, vaccine debates, and why women love true crime. The episode is laced with spontaneous humor, self-deprecating stories, and a mutual curiosity about what keeps people connected despite differences.

Key Discussion Points & Insights

1. Marriage, Individuality & “Defending Bobby”

Starts ~[02:00]

• Cheryl Hines on being criticized for her husband (Bobby Kennedy) and the importance of differentiating herself from his views.

  • “She made it plain that she doesn’t agree with everything. That’s gotta be enough when you’re in a marriage.” — Bill [08:32]
  • “A lot of people are just mad that I’m married to Bobby… People are just mad.” — Cheryl [08:57]

• Maher praises Bobby Kennedy’s willingness to stand up for beliefs despite the social or familial cost.

  • Maher notes the pain and fallout public partners face when attacked for their spouses’ opinions.

• Cheryl discusses how Bill's defense during a media controversy became meaningful to her and even made it into her book.

  “At the time, I was like, wow, this is so crazy… when you came out, I was like, oh my God, Bill, I love you.” — Cheryl [15:27]

2. The New Blacklist: Cancel Culture in Hollywood & Politics

Starts ~[15:40]

• Maher and Hines discuss how Hollywood, once the champion against the 1950s anti-communist blacklist, now enforces its own “woke” blacklist, especially against anyone seen as ideologically non-conforming.

  • “It’s a town that loves to romanticize the period in the ‘50s… but they have their own kind of blacklist now.” — Bill [16:00]

• Both bemoan “compassionate” liberals turning intolerant and mean, particularly on social media.

  • Maher and Hines agree that assuming everyone on “the other side” is evil or unworthy of dialogue is toxic.

3. Political Purity, Relationships, & The Art of Compromise

Starts ~[13:33]

• The messiness of marriage and the impossibility of agreeing with your spouse on everything.

  • “Any relationship… sometimes you just have to say, okay, I will get through this moment, and we know who we are to each other.” — Cheryl [14:25]

• Notable Quote:

  “Sometimes when you’re married, you just have to eat shit… you’re not wrong.” — Cheryl referencing Bill’s monologue [14:08–14:20]

• The hypocrisy of “anti-bullying” activists using bullying tactics themselves.

4. Meeting Trump & Dispelling Stereotypes

Starts ~[17:24]

• Both discuss surprising private encounters with Donald Trump:

  • Hines: “He really likes to listen to people. He’s very curious.” [17:49]
  • Maher: “He looked in my eye… waited until I finished. Even when it was contradictory, he never got blustery or mad about it.” [19:00]

• Maher shares the story of Trump signing his own list of previous insults directed at Maher, noting that Trump, despite his flaws, has no permanent enemies and is unexpectedly flexible.

5. Media Echo Chambers & Self-Censorship

Starts ~[49:17]

• Both critique the way partisan media covers (or omits) nuance, leading to a culture in which “we each have our own media.”

  • Cheryl says she now watches NewsNation to get both sides; Maher says he reads The New York Times and the New York Post for balance.

• Notable Quote:

  “It’s only when I read them both like, okay, now I fully understand the situation.” — Bill [49:40]

6. Women, Relationships, and the “Leather or Red” Debate

Scattered throughout; highlights around [03:15], [44:47], [53:31]

• Humorous debate around Maher’s dislike of red clothing on women and “thick, loud clothes like leather.”

  • Hines jokes: “What if you walked in, it was like red leather, head to toe?” — Cheryl [70:09]
  • Maher: “Red clothes are even worse. …all I can think of is Nancy Reagan. Republican women iconically wear red.” [43:45]

• Playful banter about wardrobe choices as political statements and personal taste.

7. Show Business, Social Status & Hypocrisy

Starts ~[67:25]

• Maher contends Hollywood is full of “very talented, not that bright” people fearful of taking risks outside the safe consensus.

  • “If we were readers, we’d be a different category. We’re actors.” — Bill [67:45]

• Both point out selective outrage, especially when political “teams” close ranks to protect their own.

8. Pandemic, Public Health, and Vaccine Skepticism

Starts ~[103:02]

• Broad discussion of how COVID policy, the “feelings vs. facts” debate, and public health messaging exposed flaws on all sides.

  • Maher recounts being labeled anti-vaxx for advocating skepticism: “I’m just pro-skepticism about anything medical.” [118:44]
  • Both lambast dismissing natural immunity and the performative aspects of public health responses.

  “There’s nothing more sort of bargain-basement medicine than natural immunity is the best.” — Bill [104:38]

• Hines: “I’m always saying to [Bobby], you have to think about people’s feelings when you’re talking about this.” [104:58]

9. The Allure of True Crime for Women

Starts ~[109:00]

• Hines explains women’s fascination with true crime as “comfort viewing” because the formula reveals the truth and delivers justice (usually the husband did it).
  • “And you go to bed feeling, like, great. And Bobby’s like, how do you feel good about the murder? …You don’t get it. You’re a guy.” — Cheryl [112:28]

10. On Age, Experience & The Limits of Change

Starts ~[129:03]

• Discussion of ageism, Biden, and whether there’s a “right” time to step aside—Maher has always been “an avenging angel against ageism,” but the Biden experience complicated his stance.
  • “So don’t automatically make a rule, like, at 75… Some people at 75 are great, some people are old at 50.” — Bill [129:29]

11. Personal Growth, Regrets, and Life’s Real Pleasures

Starts ~[75:03]

• Maher reflects: “I have probably more regrets about that part of my life [relationships] than any other part… the stupidity reigned so late.” — Bill [76:47]

• Both agree that as one matures, conversation and genuine connection rival sex as the greatest pleasures in life.

  • “I’ve said to people… I hate that I have to decide between kissing you and talking to you.” — Bill [78:03]

12. Notable Running Joke: The “Morning Show” Pitch

Recurring throughout, especially [80:06], [133:03]

• The two riff repeatedly on the idea of launching a morning talk show called “What I Did for Love,” “Fester,” “Spit Take,” or “Your Tits Look Great”—complete with gags about wardrobe, crew exhaustion, and TV stereotypes.
  • “We are destined for a morning talk show!” — Bill [86:12]
  • “That will be the name of our talk show: Your tits look great.” — Bill [93:34]

Notable Quotes & Memorable Moments

• “Liberals in theory are supposed to be compassionate. …There was nothing compassionate about what he said about you.” — Bill Maher [13:33]
• “Sometimes when you’re married, you just have to eat shit…” — Cheryl Hines [14:10]
• “The Republicans have been very kind to me from the beginning… I can’t say that for the Democrats.” — Cheryl Hines [27:11]
• “You could have waited until you saw how I reacted after the dinner, which was—I never stopped criticizing him. I have the tapes to prove it.” — Bill Maher re: Trump [13:00]
• “If you can, get with a 20 year old. …No, but I’m just saying, I don’t know what I’m saying.” — Bill Maher (laughing, on the hypocrisy of age-gap relationship judgments) [57:02]
• “Serious people talk to each other and accept that you’re gonna get to this point where you don’t agree. Again, the marriage thing—very comparable to politics.” — Bill Maher [58:45]
• “Everybody’s a monster till you talk to them.” — Bill Maher [59:44]
• “If your tits look great, let’s say it. Let’s just fucking say it.” — Bill Maher [93:31]
• (Joking about club rumors)
  Cheryl: “The rumor for so long was that you would masturbate into a sock before a show.” [87:19]

Key Timestamps for Important Segments

• [01:42] Cheryl Hines enters, discusses relationship with Bobby Kennedy, politics and marriage
• [08:17] Maher talks about standing up for Cheryl amid media attacks
• [13:33] Discussion on liberal hypocrisy & compassion
• [17:24] Maher/Hines on meeting Trump in person—unexpected experiences
• [27:11] Cheryl: Republicans’ kindness vs. Democrats' meanness
• [49:17] Media echo chambers and getting both sides
• [75:03] Personal regrets, relationships, and growth
• [78:03] “Deciding between kissing you and talking to you”
• [104:20] COVID policy, natural immunity, vaccine skepticism
• [109:00] Why women love true crime
• [129:03] Ageism, Biden, and experience
• [133:03] The “morning show” running joke
• [142:46] Bill Maher on obesity, health, and COVID

Tone & Takeaways

The episode is fast-paced, improvisational, and deeply personal with both Maher and Hines sharing self-reflection, life lessons, and plenty of off-color humor. Instead of avoiding tough or controversial subjects (marriage strife, political tribalism, the pandemic, cancel culture), the conversation underscores the virtue of curiosity, the necessity of compromise, the dangers of groupthink, and the value of authenticity—even (or especially) when it’s messy.

Cheryl and Bill demonstrate that dialogue, even about hot-button issues, can be civil and illuminating when mutual respect and humor are present.

Final Note

A quintessential Club Random episode: probing, irreverent, intimate, and effervescent—a reminder that the best conversations weave together deep truths and big laughs.