The Rewatchables: ‘Brokeback Mountain’ With Bill Simmons and Wesley Morris

Released on July 29, 2025

Introduction and Studio Banter

The episode begins with playful exchanges between host Bill Simmons and guest Wesley Morris, highlighting their camaraderie and teasing about Wesley's newly launched podcast, Cannonball. Transitioning seamlessly, they introduce the episode's focus on Ang Lee's Brokeback Mountain, setting the stage for an in-depth discussion.

Reflections on Brokeback Mountain

Brokeback Mountain, released in 2005, is commemorated on its 20th anniversary. The hosts delve into the film's enduring impact, particularly Heath Ledger's poignant performance and its significance in shaping both his career and the portrayal of LGBTQ+ relationships in mainstream cinema.

Heath Ledger and Jake Gyllenhaal’s Performances

Bill Simmons praises Ledger's portrayal of Ennis Del Mar, noting, "the Heath Ledger performance was the thing that jumped out because it's such a great performance” [04:12]. Wesley Morris reflects on his younger self's perception, admitting initial disappointment with the film's subtlety: "I was disappointed that there wasn't more fucking... because I was young and single... I want a hotter movie” [05:33]. However, revisiting the film years later, Morris acknowledges the depth and patience in Ledger and Gyllenhaal's performances. He states, "this movie is such a patient movie that is so much more about, like, being able to love” [06:39].

Oscar Controversy: Ledger vs. Hoffman

A significant portion of the discussion centers around the 2006 Oscars, where Philip Seymour Hoffman won Best Actor for Capote, while Ledger's exceptional performance in Brokeback Mountain was overlooked. Simmons expresses frustration, saying, "We had to litigate how dumb that was. It was dumb when it happened. It was fucked up, and it shouldn't have lost” [52:35]. Wesley Morris concurs, emphasizing the quality of both performances and the unmerited nature of Crash's win over Brokeback Mountain.

Character Analysis: Ennis Del Mar and Jack Twist

The hosts dissect the complexities of the main characters. Simmons observes, "Jack Twist is clearly gay” [15:30], contrasting with Ledger’s Ennis, whose internal struggle with his sexuality is palpable. Morris highlights the subtlety of Ennis's character, noting Ledger’s ability to portray a man grappling with his identity: "Ennis is trying to get out of the rope.” [26:00]. They discuss pivotal scenes, such as the first meeting outside the trailer and the tent scene, emphasizing the actors' nuanced performances and the film's masterful choreography.

Director Ang Lee’s Vision

Ang Lee's directorial prowess is lauded for creating an environment where the characters' relationship unfolds organically. Morris remarks, "It's such a beautiful and sweet ending," referencing the film's final moments [135:45]. Simmons appreciates Lee's ability to trust the audience, allowing periods of silence and natural interaction without forced dialogue or cinematic embellishments. He states, "people just have to... we have to... trust us to be able to follow the beats” [35:13].

Impact on Actors’ Careers

Ledger's role in Brokeback Mountain is seen as a turning point, solidifying his reputation as a versatile actor capable of profound emotional depth. Simmons muses on the potential trajectory of Ledger's career had he not tragically passed away, suggesting he could have dominated both indie and blockbuster cinema with roles like the Joker in The Dark Knight [42:04]. Gyllenhaal's career is also discussed, with Simmons noting his ability to reinvent himself through diverse roles, though he laments the unpredictability of Hollywood's reception [49:53].

Legacy and Cultural Significance

Brokeback Mountain is celebrated for breaking ground in LGBTQ+ representation, presenting a love story set against the rugged backdrop of the American West. The hosts argue that its specificity—focusing intensely on Jack and Ennis—renders it universally relatable. Simmons compares its patient storytelling to the works of Bergman, while Morris contemplates its place among the first 25 influential movies of the first quarter of the 21st century [21:26].

Awards and Categories Highlighted in the Podcast

Throughout the episode, Simmons and Morris engage in playful award categorizations, humorously awarding elements like:

• Wheat Rig Award for Most Cinematic Shot: They mention the film's meticulous framing, particularly Heath Ledger and Jake Gyllenhaal's chemistry.

• Hottest Take Award: Simmons contends that Ledger's performances rank among the best of the century, a sentiment reaffirmed by fellow actors like Daniel Day-Lewis [141:21].

• Mount Rushmore of Ennis Del Mar’s Worst Movie Husbands: A comedic segment where they critique fictional characters as part of their playful awards.

These segments add levity while underscoring the film's memorable moments and performances.

Production Insights and Anecdotes

The conversation reveals behind-the-scenes challenges, such as Ledger's intense method acting leading to injuries during filming: "Ennis throws up and punches the wall a couple times, which apparently he did in real life and wasn't supposed to” [61:03]. They also discuss Michelle Williams' dedication to her role, including requesting multiple takes for pivotal scenes to capture the desired emotional depth [113:49].

Alternate Casting Speculations

Simmons and Morris entertain "what if" scenarios, imagining how Brokeback Mountain might have differed with other actors like Matt Damon, Joaquin Phoenix, or Tom Cruise. They ponder the chemistry and authenticity Ledger and Gyllenhaal brought, asserting that such performances are rare and potentially unrepeatable with different casts [76:08].

Editing and Storytelling Techniques

They praise Ang Lee's editing choices, particularly the seamless integration of multiple takes and perspectives, which contribute to the film's emotional ambiguity and depth. Morris notes, "the ambiguity is what is the strength of the scene and why it's heartbreaking” [138:07], emphasizing how these techniques enhance the storytelling.

Final Thoughts and Legacy

Bill Simmons concludes by reflecting on Ledger's enduring legacy as an actor who delivered unforgettable performances in a tragically short career. Morris echoes this sentiment, appreciating how Brokeback Mountain remains a testament to beautiful, flawed love against societal constraints. They agree that the film's balance of personal struggle and cinematic artistry ensures its place as a rewatchable classic.

Notable Quotes:

• Bill Simmons: "the Heath Ledger performance was the thing that jumped out because it's such a great performance” [04:12]
• Wesley Morris: "this movie is such a patient movie that is so much more about, like, being able to love” [06:39]
• Bill Simmons: "We had to litigate how dumb that was. It was dumb when it happened. It was fucked up, and it shouldn't have lost” [52:35]
• Wesley Morris: "the ambiguity is what is the strength of the scene and why it's heartbreaking” [138:07]

Conclusion

In this comprehensive discussion, Bill Simmons and Wesley Morris celebrate Brokeback Mountain as a landmark film that redefined romantic storytelling and LGBTQ+ representation in cinema. They highlight the exceptional performances of Heath Ledger and Jake Gyllenhaal, critique the controversial Oscar outcome, and admire Ang Lee's directorial finesse. The episode serves as both a nostalgic homage and a critical examination of a film that continues to resonate deeply with audiences decades after its release.