Podcast Summary: Fly on the Wall with Dana Carvey & David Spade
Episode: RE-RELEASE – Sheryl Crow
Date: August 20, 2025
Guests: Sheryl Crow
Hosts: Dana Carvey, David Spade
Overview
This episode features a candid and wide-ranging conversation between comedians Dana Carvey and David Spade and nine-time Grammy-winning singer-songwriter Sheryl Crow. From memories on SNL and wild Hollywood parties to reflections on fame, songwriting, parenting, and celebrity culture, Sheryl opens up about her life and career. The trio also bond over their mutual admiration for music (especially The Beatles), share behind-the-scenes anecdotes with legends like Michael Jackson and Mick Jagger, and riff on parenting in a social media world. Packed with stories, humor, and warmth, this episode is as much about the absurdities of show business as it is about finding authenticity amid the hype.
Key Discussion Points & Highlights
Reuniting and First Impressions
[03:14]
- Sheryl exclaims it's been "3,000 years" since she last saw Dana and David, recalling the SNL 40th anniversary in 2016.
- Hosts intro Sheryl's massive career: "32 Grammy nominations, nine wins, and 50 million albums."
[03:36] Dana: "Just to remind everyone what the fuck is going on right now."
Sleep Paralysis, Supernatural Experiences, and Nashville
[04:48]–[07:02]
- Sheryl and Dana bond over both having sleep paralysis.
Sheryl: "For a long time, I would have it almost every night...sometimes on airplanes." - Light banter about Nashville ("full of ghosts"; Civil War history).
Wild Hollywood Parties and Salman Rushdie
[07:30]–[09:20]
- Sheryl shares a wild party story: She and Minnie Driver once threw a New Year's Eve party that ballooned from 80 to 800 guests, including Salman Rushdie who had a bounty on his head.
- Describes her old LA compound and why she eventually left for family-focused life.
Past Circles & Musician Tribes
[09:20]–[10:23]
- Recollections of celebrity peer groups—Courtney Cox, Kid Rock, and the fun (and chaos) of hangouts during the "Joe Dirt" era.
- David watched Sheryl’s recent documentary, calling it “a tearjerker.”
Reflections on Fame, Critical Voices, and Parenting
[13:42]–[17:46]
- Sheryl on 'love-hate' with fame:
Sheryl [14:03]: "I've always looked at my life as, okay, how am I going to fuck this up?"- Fame is both pressure and a "mind trip."
- She's always been "uber critical" of herself and fame made her panic about being "cool" or "included.”
- Dana echoes the watershed nature of health or family events:
"In that moment, everything got real clear." - Sheryl avoids social media for her mental health; her kids' access is tightly limited ("I would be distraught").
Parenting, Tech, and the Meaning of Success
[17:46]–[21:00]
- Discussion on keeping kids off social media; the struggle of tech boundaries.
- Dana acknowledges how screen time can be an endless battle.
Woodstock '99 and Performance Chaos
[21:00]–[23:23]
- Sheryl's recollection of the disastrous Woodstock ’99:
Sheryl: "At one point, shit landed on my hand while I was playing bass during 'My Favorite Mistake.' That’s when we stopped. We played about four songs." - Joke riffing on following up Insane Clown Posse and Andy Dick.
On Musicianship, Songwriting, and Career Origins
[24:34]–[26:20]
- Sheryl recounts landing a job as Michael Jackson’s backup singer by brazenly showing up for an audition without a recommendation:
Sheryl [25:50]: "I said, I'm Sheryl Crow. I am not recommended. But I overheard Daryl Finesse... They said, well, come on in." - Early career included jingle sessions before the Jackson tour.
Performing with the Greats: Mick Jagger, Michael Jackson
[30:15]–[32:17]
- Sheryl: Mick Jagger was far more intimidating than Michael Jackson.
Sheryl: "By the time I got to sing with them...that was the bomb. I was so afraid, I threw up all day." - Describes “out of body” experience performing on stage, enduring self-doubt despite huge gigs.
- The parallel struggle of comedians and musicians with self-critique.
Tabloids, Public Scrutiny, and Dating in the Spotlight
[39:42]–[41:38]
- Sheryl reflects candidly on tabloid frenzy while dating Lance Armstrong, and why some relationships attract more attention than others.
- Surprising fact: She went to college with Brad Pitt and knows him to be genuinely kind, despite relentless press scrutiny.
The Pressures and Double Standards of Ambition
[45:55]–[47:56]
- Sheryl on cultural differences in ambition's perception:
Sheryl: "For women, the idea of an ambitious woman is such a turn off..."- She encourages her sons to value hard work for its own sake, not just for "being famous."
- She laments the change in celebrity culture, where success doesn't always equate to hard work.
The Economics of Music & Song Catalogs
[54:12]–[56:49]
- Dana asks about artists selling their catalogs.
Sheryl reveals she sold her "catalog," not her songwriter’s share, a few albums ago:
"Everything was going to streaming...it's just ridiculous...100% of a penny is still going to be a penny." - Discusses the financial shift from albums to streaming and song placements.
The Lasting Power of Songs & The Beatles
[58:09]–[61:17]
- Sheryl marvels at new generations knowing her songs:
Sheryl: "My manager started talking about, and now you're a legacy artist. And I'm like, oh..." - Deep dive on the influence of The Beatles in songwriting.
- Dana & David recount interviewing Paul McCartney and the process of Beatles songmaking.
The Mystery and Magic of Creativity
[64:03]–[65:14]
- Sheryl on creativity:
Sheryl: "There are moments where you go, okay, you can’t define what creativity is...you're tapping into something."
SNL Memories & On-Stage Self-Loathing
[66:42]–[68:06]
- Sheryl jokes about needing to sleep with Lorne Michaels for SNL invites.
- Everyone empathizes with the post-performance "fetal position" syndrome—even after seemingly great shows.
Song “Picture” with Kid Rock & Karaoke Fame
[69:18]–[72:18]
- David calls "Picture" "so fucking good." Sheryl explains Kid Rock was the driving force in the studio and live gigs together were unpredictable, but fun.
Dream Supergroups & Admired Female Musicians
[72:38]–[74:05]
- David and Dana challenge Sheryl to assemble her Travelling Wilburys-style female supergroup: Sheryl: “Stevie Nicks, Brandi Carlile, Bonnie Raitt, Emmylou Harris, Linda Ronstadt... there’s a lot of good young female music out there, too.”
TikTok, Relevance, and Pop Culture
[75:05]–[76:15]
- Anecdotes about label pressure to join TikTok, with the generational conflict:
Sheryl: "My 12-year-old was like, mom, please don’t. That is so cringy."
Classic Comedy, Family, and Legacy
[76:19]–[78:01]
- Light jokes about generational comedy (Chop Broccoli, Joe Dirt, Wayne’s World).
- Plans for all three to hang out in Nashville, do more music and comedy gigs.
Closing Reflections: Age, Wellness, and Longevity
[80:17]–[81:18]
- Sheryl on feeling young:
Sheryl: “I feel like I’m in my 20s... as far as your listening audience knows, I look like I’m in my 20s. There, I said it.” - Admits fitness is largely genetics:
“I’m from a long line of wiry and fit...petite, wiry people.” - David: "Your voice is still raspy and sexy. And then your singing is still perfect…”
Notable Quotes & Moments
- Sheryl Crow on fame:
"[Fame is] a real mind trip... I’ve always looked at my life as, okay, how am I going to fuck this up?" [14:03] - Sheryl on self-doubt:
"You have to show up and be fearless. But as soon as you walk offstage, you go, 'Oh my God, I suck…'" [31:44] - On Woodstock '99:
"Some [excrement] landed on my hand while I was playing bass during 'My Favorite Mistake.' That’s when we stopped." [22:57] - Sheryl on ambition and double standards:
"The idea of an ambitious woman is such a turn off...but for a woman to be ambitious, it's still problematic." [45:55] - On the mystery of creativity:
"You can't really define what inspiration is, but it is a real thing." [64:37] - David Spade on 'Picture':
"It blew the fuck up. Is that possible?" [69:52]
Timestamps for Major Segments
- 00:00–02:43 | Opening banter, intro, and Sheryl’s call-in from Nashville
- 03:14–06:45 | Sleep paralysis, supernatural Nashville
- 07:30–09:20 | Hollywood parties, Salman Rushdie story
- 09:20–11:48 | Peer groups, documentary talk, Top Gun, raising kids
- 13:42–17:46 | Navigating fame and the pressure of self-doubt
- 17:46–21:00 | Parenting, tech, and generational change
- 21:00–23:23 | Woodstock 1999 horror stories
- 24:34–26:20 | Breaking into Michael Jackson’s band
- 30:15–33:41 | Fearlessness on stage with legends, creative insecurity
- 39:42–41:38 | Tabloid culture, relationships, and Brad Pitt stories
- 45:55–47:56 | Ambition and its perception for women
- 54:12–56:49 | The business of song catalogs, streaming, and money
- 58:09–61:17 | Legacy, new generations, and The Beatles
- 64:03–65:14 | Magic of creativity and inspiration
- 66:42–68:06 | SNL memories, post-show self-loathing
- 69:18–72:18 | "Picture" with Kid Rock and karaoke canon
- 72:38–74:05 | Assembling a female supergroup
- 75:05–76:15 | TikTok, pop-culture adaptation
- 80:17–81:18 | Wellness, longevity, and closing jokes
Closing Tone
The conversation is warm, self-deprecating, and occasionally poignant, mixing industry insight and life lessons with comedic timing and affection. Sheryl emerges as authentic and grounded, balancing stardom with relatability. Both Dana and David elevate the banter with sharp wit and heartfelt curiosity.
Sheryl Crow:
"Hey, this is the best podcast I’ve ever done, ever." [78:28]
For listeners and fans, this is a must-hear dive into not only Sheryl Crow’s remarkable life, but the quirks, struggles, and joys of everyone who works in the trenches of entertainment.