The Bert Show: Vault – Jake Gyllenhaal Joins The Show

Date: January 22, 2026
Host: The Bert Show Cast
Featured Guest: Jake Gyllenhaal

Overview

This lively episode of The Bert Show spotlights a candid conversation with actor Jake Gyllenhaal during his promotion of the film Jarhead. The hosts take Jake through a mix of film career analysis, rumors about his relationship with Kirsten Dunst, and plenty of light-hearted off-topic banter—showcasing both the charm of the show and their guest. With characteristic authenticity, the hosts probe into career choices, personal life, and even head size, delivering laughs and thoughtful moments throughout.

Key Discussion Points & Insights

Jake Gyllenhaal’s Career Choices and Approach to Roles

• Preference for Indie Films Over Blockbusters

  • Jake shares why independent roles have drawn him in:
    • “They're just for me. They were just the best ones, you know, really... ones where I could, like, stretch myself and push myself.” (01:53, Jake)
    • He embraces both indie and blockbuster films, emphasizing it's not about salary but artistic satisfaction. (02:18–02:51)

• Blockbuster Ambitions and Enjoyment

  • Loves the spectacle and excitement of big-budget movies, like The Day After Tomorrow:
    • “I like running away from things, so you know, I like them both.” (02:37, Jake)

• Notable Roles He Didn’t Get

  • Close to starring in Moulin Rouge!:
    • “I really would have liked to do Moulin Rouge... me, Heath and Ewan McGregor up for that role.” (03:05, Jake)
    • Shares a personal story of friendship with Heath Ledger stemming from auditioning for the same part.

“Brokeback Mountain” and Navigating Cultural Stigmas

• Motivation for Taking the Role
  • Jake addresses media and community reaction candidly:
    • “The thing about that film is I think it has a stigma on it already as being sort of the gay cowboy movie. And I think it's much more than that.” (03:42, Jake)
    • He reiterates no one tried to dissuade him from the part, celebrating the story’s impact and significance. (03:42–04:13)

The Kirsten Dunst Relationship Rumors

• Tabloid Frenzy and Non-Commital Answers

  • The hosts press Jake about his on-and-off relationship with actress Kirsten Dunst. Jake remains playful but protective:
    • “She's such an amazing, amazing girl and is always in my life no matter what.” (04:30, Jake)
    • Multiple attempts to get a definitive answer are rebuffed:
      • “I'll let you know next time.” (05:52, Jake)

• Advice to Young Actors About Dating

  • Jake recommends following genuine feelings, but cautions:
    • “It's usually better to date maybe outside, I would say.” (05:46, Jake)

On “Jarhead” and Its Unique War Story

• What Makes Jarhead Different

  • Explains it isn’t a typical war movie:
    • “There was a lot of waiting around and... experiences... besides the combat action.” (06:14, Jake)
    • Calls it “pretty true to life” for the Gulf War—more introspective than action-based.

• Memorable Analogy about the Film

  • Jake gives a striking comparison:
    • “I liken the movie to, like, really great sex without an orgasm.” (07:17, Jake)
    • The hosts react in typical Bert Show fashion.

Light-Hearted Moments & Running Gags

• Big Head Bantz
  • Comparison of head sizes with host Jeff Dollar erupts into jokes about fitted hats and car covers:
    • “You know, I just go to the store... and I'm just like, give me the biggest thing you got.” (09:12, Jake)
    • “You can put a car cover on me, and it looks like a Yamaha, dude.” (09:34, host)
• Host-Jake Chemistry
  • Frequent playful prodding about relationships (“Are you dating Kirsten Dunst?”) creates running comedy through the episode.

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 01:53 | Jake | “They're just for me. They were just the best ones, you know, really... where I could, like, stretch myself and push myself.” | | 02:37 | Jake | “I like running away from things, so you know, I like them both.” | | 03:05 | Jake | “I really would have liked to do Moulin Rouge! ...me, Heath and Ewan McGregor up for that role.” | | 03:42 | Jake | “The thing about that film is I think it has a stigma on it already as being sort of the gay cowboy movie. And I think it's much more than that.” | | 04:30 | Jake | “She's such an amazing, amazing girl and is always in my life no matter what.” | | 05:46 | Jake | “It's usually better to date maybe outside, I would say.” | | 07:17 | Jake | “I liken the movie to, like, really great sex without an orgasm.” | | 09:12 | Jake | “You know, I just go to the store... and I'm just like, give me the biggest thing you got.” |

Timestamps for Key Segments

• 00:00 – 01:20: Introduction and rundown of Jake’s career
• 01:21 – 03:20: Jake on indie vs. blockbuster films, roles he missed out on
• 03:21 – 04:13: Conversation about Brokeback Mountain and public perception
• 04:14 – 05:52: Pressing on Kirsten Dunst rumors, Jake’s relationship philosophy
• 06:02 – 07:34: All about Jarhead—the story, expectations, and Jake’s unusual analogy
• 07:35 – 09:41: Lighthearted banter about head sizes and hat shopping

Tone & Atmosphere

• The interview is relaxed, playful, and peppered with the Bert Show’s signature humor.
• Jake Gyllenhaal is personable, open, and quick-witted, deftly balancing honest answers with on-brand ambiguity—especially about his love life.

For Listeners Who Missed the Episode

If you’re looking for insights into Jake Gyllenhaal’s mindset as an actor, a wry candid take on old Hollywood rumors, and a hearty dose of morning show mischief, this episode is a treat. Though the hosts repeatedly try to pry into Jake’s personal life, he remains gracious, sharing thoughtful reflections on his career, motivations, and latest projects, while matching the cast’s banter step-for-step.