Sunday Sitdown with Willie Geist: Will Ferrell Talks Decades of Comedic Roles and His Favorite SNL Sketches

Release Date: August 17, 2025
Host: Willie Geist
Guest: Will Ferrell

Overview

In this engaging episode, Willie Geist sits down with iconic comedian and actor Will Ferrell at a restaurant near Rockefeller Center. Their wide-ranging conversation covers Will’s new film with Reese Witherspoon, heartfelt insights into his Will & Harper documentary, reflections on his early comedy days and SNL, his approach to memorable movie roles, and the enduring cultural impact of his performances. The tone is light, self-deprecating, and warm, peppered with laughter and signature Ferrell humor.

Key Discussion Points & Insights

1. Will Ferrell’s New Film: Working with Reese Witherspoon

(03:39–09:07)

• Film’s Premise: Two couples accidentally book the same destination wedding; Ferrell and Witherspoon star as the contrasting parents.
• Genesis: Nick Stoller, a longtime friend, pitches the movie, which begins as a simple, funny concept (03:55).
  • Memorable moment: Stoller’s “maniacal laughter” after pitching the wedding premise.
• Casting Reese Witherspoon: Both stars wanted to work together. Ferrell praises her comedic roots and their instant chemistry (05:13).
  • “The funniest things are executed by committing to the character. No matter how silly the premise is, you have to believe that you’re doing it for real.” – Will Ferrell (05:51)
• About His Character, Jim: A single dad, devoted to his daughter, skilled at “hair, makeup, and baking,” returning to a significant family location (06:24).
• Film’s Tone: Balances nostalgia with unexpected emotional depth; rated R mainly for language (07:30).
• Ferrell’s Current Criteria for Roles: Seeks projects with people he admires and unique spins – does it “feel different?” (07:56)
• Humor and Heart: The famed “emotional touchstone” scene involves wrestling an alligator (08:54).

2. "Will & Harper" Documentary: Friendship, Transition, and Kindness

(09:08–19:32)

• Story: Chronicles Ferrell’s cross-country trip with longtime friend and SNL writer Harper Steele after her transition at age 59 (09:36).
• Harper’s Announcement: Email subject line: “Here’s a weird one” (09:36).
  • “In some ways it’s really sad it took me this long…in other ways it’s so beautiful that my psyche wasn’t allowing me to suppress this anymore.” – Will Ferrell (09:52)
• Purpose: To support Harper, and explore how America receives her as a trans woman; also to learn and ask questions on behalf of curious or nervous allies (11:55).
  • “She makes it really clear: ask me anything…if you make a mistake in the way you’re asking, just ask.” – Will Ferrell (12:19)
• On-the-Road Experiences: Encountered far more kindness than hostility; “for most people, their resting place is kindness” (13:35).
  • Touching Grand Canyon moment: a retired therapist shares her own regrets about counseling a trans patient (14:17).
• Filmmaking Doubts: Initially believed “nothing happened,” but it turned out to be a powerful story (15:57).
• On Risk and Political Conversation: Ferrell acknowledges risk due to politicization but wanted to support his friend and follow his instincts (17:32).
  • “If no one wants to watch my movies…that’ll be a good one to go out on.” – Will Ferrell (17:37)
• SNL-style moments: Filming in disguise in Vegas leads to comedic mishaps, like a mustache falling off (19:20).

3. Early Years and Finding Comedy

(21:22–27:03)

• Family Life: Raised in suburban California by a musician father and teacher mother; did not view entertainment as a stable path.
• Comedy’s Role: Always loved making friends laugh, but initially pursued “real jobs” (bank teller, sports journalism) out of caution (21:56).
  • “I’d rather do standup comedy on the Tonight Show naked than go to work today.” – Will Ferrell quote about bank teller nerves (23:54)
• Bank Teller Stories: Recalls fumbling with money counts, being the worst teller, leading to “character building moments” (24:50).
• Deciding to Try Comedy: Took a Groundlings improv class to scratch an itch. Quickly realized he’d found his calling (26:25).
  • “There was no…it does not feel like work to me…this is what I want to do.” – Will Ferrell (26:25)

4. Saturday Night Live: Auditions, Fame, and Favorite Sketches

(27:03–37:59)

• SNL Audition: Intimidating, surreal experience; required to impersonate celebrities to an empty studio (27:21).
  • “You could run right now. You could just get in the elevator and go back.” – Will Ferrell (27:55)
  • Second audition: improvised a surreal cat toy bit, trusting his comedic instinct (29:19).
• The Briefcase Bit: Intended to impress Lorne Michaels by bringing fake money, but never had the right moment (29:55).
  • “The tone is not fun and games…what comedian carries a briefcase?” – Will Ferrell (30:18)
• Memorable SNL Characters: Cheerleaders, Dubya, cowbell guy, “old prospector,” “the lovers” with Rachel Dratch.
  • Overlooked Favorite: Old Prospector. Born from index-card challenges with Harper Steele: “You need to write that sketch,” Harper prompted (33:43).
  • Lovers “hot tub professors” sketch: aim was “to make the other people break” (34:46).
• Leaving SNL: Hard, scary decision. At first, Hollywood prospects were uncertain; took a “leap of faith” (35:11).
  • “If someone had said…you only get to do Saturday Night Live, I would have signed on the dotted line.” – Will Ferrell (35:14)
• Breakthrough Films: Old School, Elf, Anchorman—none were locked in when he left (37:02).

5. Movie Legacy and the Art of the Fool

(40:28–47:15)

• Signature Roles: Anchorman, Talladega Nights, The Other Guys, Old School, Elf, Step Brothers.
• Comic Thread: Plays “the guy next door” with a “rug pull”—audiences relate to him and are surprised by his outrageousness (40:47).
  • “I’m like the guy who lives next door that you don’t think I’m gonna say the things that I say. And that is the rug pull that has worked for me.” – Will Ferrell (40:51)
• Central Archetype: Men with unwarranted, supreme confidence fascinate him: “Ron Burgundy, Ricky Bobby…” (42:13).
• Legacy Quotes: Frequently cited lines include:
  • “Did we just become best friends?” (Step Brothers)
  • “You’re my boy, Blue!” (Old School)
  • “Buddy the Elf, what’s your favorite color?” (Elf)
  • "Shake and bake," “Milk was a bad choice,” “Glass case of emotion,” “Stay classy,” “Go f yourself, San Diego.”
  • “People will yell things I don’t recognize as a quote from my movie.” – Will Ferrell (42:50)
• Audience Love: Ferrell delights in stories of families quoting him, and gentle ribbing about earning royalties for catchphrases (44:21).
• Public Persona: Not “on” all the time, but loves occasional outlandish public appearances (e.g., Buddy the Elf at a LA Kings game, Conan with a parrot, the nunchuck cameo in Wedding Crashers) (45:08, 46:19).
  • “It’s just fun to still be out in the world and do weird stuff like that.” – Will Ferrell (45:58)

Notable Quotes & Memorable Moments

• On Commitment to Characters:
  • “You don’t wink at the camera ever, even if you’re going off a cliff.” – Will Ferrell (06:02)
• On the "Will & Harper" Road Trip:
  • “For most people, their resting place is kindness…when you really sit down and have a conversation, it becomes less mystical, less scary.” – Will Ferrell (13:36)
• SNL Audition Pressure:
  • “You could run right now. You could just get in the elevator and go back.” – Will Ferrell (27:55)
• Iconic Movie Quote Interactions:
  • “People just get mad at me…‘Why are you so sweaty?’ I was riding a bike! ‘No, from Step Brothers!’” – Will Ferrell (42:50)

Highlighted Timestamps

• 03:39 — Discussing new movie premise, casting, collaborating with Reese Witherspoon
• 09:36 — Harper Steele’s coming out email; the beginning of “Will & Harper”
• 13:35 — Discovering kindness across America during their documentary road trip
• 17:32 — Weighing the “risk” of participating in a transgender visibility project
• 21:56 — Ferrell’s childhood, suburban upbringing, and attraction to comedy
• 27:21 — SNL audition story, surreal empty studio
• 29:55 — The “briefcase of fake money” bit for Lorne Michaels
• 33:43 — Old Prospector and The Lovers: favorite SNL sketches
• 35:11 — The difficult leap from SNL to Hollywood
• 40:47 — The thread through his beloved movie characters
• 42:13 — The character archetype: “supreme but unwarranted confidence”
• 44:21 — Family-quoted lines, “breakfast of champions” moment
• 45:58 — Enjoyment of doing eccentric public appearances

Tone & Atmosphere

The episode feels like a back-and-forth between old friends, filled with Ferrell’s trademark dry wit and Geist’s genuine admiration. Ferrell is candid about career doubts, grateful for his success, and always ready to undercut himself with a self-effacing joke. The mood remains warm, informal, and celebratory throughout.

Useful For:

• Fans seeking a deep-dive into Will Ferrell’s career and creative processes
• Those interested in behind-the-scenes SNL stories and comedic development
• Viewers wanting insight into the making and purpose of “Will & Harper”
• Anyone looking to better understand the evolution of modern American comedy through one of its icons