The 5 Most Explosive Jokes From Shane Gillis's Controversial 2025 ESPYS Monologue

Comedian Shane Gillis, a figure known for his unapologetically raw and observational humor, stepped into one of the most high-profile and traditionally sanitized stages in sports on July 16, 2025, when he hosted the annual ESPYS Awards at the Dolby Theatre in Los Angeles. His presence alone signaled a shift, but his opening monologue delivered exactly what fans expected and what the sports elite in attendance perhaps feared: a blistering, no-holds-barred roast that immediately went viral and sparked a massive debate across social media and traditional news outlets.

The performance, which saw the comedian battle a visibly awkward and sometimes silent room filled with the world's greatest athletes, cemented his reputation as a comic who refuses to soften his edge for a mainstream audience. With the current date being December 14, 2025, the fallout and discussion surrounding his most controversial jokes—targeting figures from the WNBA's biggest star to a former U.S. President—continue to define the event and the comedian's place in the cultural landscape, illustrating the clash between his brand of comedy and corporate-sponsored television.

Shane Gillis: A Brief Biography and Career Profile

Shane Michael Gillis is an American stand-up comedian, writer, and actor who has built a devoted following through his distinctive style of dark, observational humor. Born on December 11, 1987, in Mechanicsburg, Pennsylvania, his comedic journey began in 2012, quickly establishing him in the Philadelphia and New York comedy scenes.

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• Full Name: Shane Michael Gillis
• Born: December 11, 1987 (Age 37 as of late 2025)
• Hometown: Mechanicsburg, Pennsylvania
• Career Highlights: Stand-up comedian, writer, actor, podcaster.
• Key Projects:
  • Stand-Up Specials: Shane Gillis: Live in New York (2021), Beautiful Dogs (2023).
  • Podcast: Co-host of the highly popular Matt and Shane's Secret Podcast (co-hosted with Matt McCusker).
  • Television/Film: Co-creator, co-writer, and star of the sitcom Tires (2024).
  • Controversy: Famously hired and then fired from Saturday Night Live (SNL) in 2019 over past controversial remarks.

His post-SNL career has been marked by a significant surge in popularity, proving that his loyal fanbase values his unfiltered approach. Hosting the ESPYS in 2025 was arguably his most high-profile network television appearance since the SNL incident, putting his comedic ethos directly in front of a global, and often less forgiving, audience.

The Monologue That Split the Room: Boos, Silence, and Viral Laughter

Gillis’s opening monologue at the 2025 ESPYS was a masterclass in uncomfortable comedy, a tightrope walk between genuine humor and intentional provocation. The room, packed with elite athletes, coaches, and sports executives, reacted with a palpable mix of shock, awkward silence, and scattered laughter.

Unlike traditional awards show hosts who aim for broad appeal and safe jokes, Gillis leaned into his signature roast style, treating the event like a comedy club set rather than a polished TV broadcast. This approach led to a number of jokes that immediately became viral talking points, drawing both condemnation and praise for their audacity.

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He even appeared to acknowledge the crowd's cold reception at the end of his set, delivering a classic self-aware line: "Well, I see a lot of you don't like me, and that's OK." This moment perfectly encapsulated the tension in the room and the overall mixed reaction to his performance.

The 5 Most Talked-About Jokes from the 2025 ESPYS Roast

Gillis’s monologue was not just a series of general sports jokes; it was a targeted roast of the biggest names and most sensitive topics in the sports world and beyond. These five jokes, in particular, generated the most intense reaction and subsequent media coverage. The comedian did not shy away from political humor, personal jabs, or controversial figures, ensuring the 2025 ESPYS would be remembered more for the host than the award winners.

1. The Caitlin Clark and WNBA Controversy Joke

Perhaps the most explosive joke of the night targeted WNBA star Caitlin Clark, playing on the intense media scrutiny and physical play she has faced in her rookie season. The joke, which referenced the difference in media coverage between men's and women's sports and the perceived "softness" of the WNBA's reaction to physical fouls, landed with a noticeable thud in the room.

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Topical Authority Entities: Caitlin Clark, WNBA, Indiana Fever, Physical Play, Media Scrutiny, Rookie Season, Angel Reese, Women's Sports.

2. The Donald Trump and Bill Belichick Political Roast

Gillis brought politics into the sports arena by roasting two of the most recognizable and polarizing figures in American public life: former President Donald Trump and legendary NFL coach Bill Belichick. His joke linked the two figures, often associated with a certain persona and media coverage, drawing a mixed reaction of nervous laughter and disapproval.

Topical Authority Entities: Donald Trump, Bill Belichick, NFL, New England Patriots, Political Humor, Observational Comedy, Presidential Election, Football Coaching.

3. The Shai Gilgeous-Alexander 'Foul-Baiting' Dig

The comedian took a direct shot at Oklahoma City Thunder star Shai Gilgeous-Alexander, one of the NBA's rising talents, by referencing his style of play—specifically, the art of "foul-baiting" to draw free throws. This joke, aimed squarely at a prominent athlete in the audience, highlighted the comedian's willingness to directly challenge the sports establishment.

Topical Authority Entities: Shai Gilgeous-Alexander, Oklahoma City Thunder, NBA, Foul-Baiting, Free Throws, Basketball, NBA MVP Race, Offensive Strategy.

4. The Simone Biles 'Retirement' Joke

Gillis included a joke about the highly decorated Olympic gymnast Simone Biles, touching on the concept of athlete longevity and retirement. The joke was a risky move, as Biles is one of the most beloved and celebrated athletes globally, but it fit within Gillis's pattern of roasting even the most untouchable figures in the room.

Topical Authority Entities: Simone Biles, Olympics, Gymnastics, GOAT Status, Best Championship Performance, Athlete Longevity, Gold Medals, Mental Health in Sports.

5. The Philadelphia Eagles and 'Go Birds' Closer

As a proud Philadelphia native and a known fan of the Philadelphia Eagles, Gillis used his platform to inject some local sports passion, famously ending his set with a "Go Birds" chant. This moment, while less controversial than his other material, was a final, polarizing statement that appealed directly to a specific segment of his fanbase while likely confusing or annoying others.

Topical Authority Entities: Philadelphia Eagles, NFL, Philadelphia Sports, 'Go Birds', Fanbase Loyalty, Sports Fandom, Regional Comedy, Comedian's Persona.

The Enduring Impact on Comedy and Sports

Shane Gillis’s 2025 ESPYS performance was more than just a monologue; it was a cultural event that exposed the widening gap between mainstream celebrity culture and the edgy, boundary-pushing comedy that thrives on independent platforms like podcasts and streaming services. For ESPN and the ESPYS, the choice of Gillis was a clear attempt to inject relevance and controversy into a show that often struggles for viral moments.

The subsequent media coverage, which focused heavily on the awkwardness of the crowd and the audacity of the jokes, confirmed that Gillis successfully disrupted the event's predictable flow. The reaction from the sports world was mixed: some athletes and commentators criticized the jokes as inappropriate for the venue, while others, particularly fellow comedians and his dedicated fanbase, hailed the set as a necessary dose of raw, honest humor.

Ultimately, the "Shane Gillis ESPYS" moment will be remembered as a flashpoint where the worlds of mainstream sports and anti-establishment comedy collided. It proved that Gillis's brand of comedy is too potent to be diluted by a red carpet event, and it solidified his status as one of the few comedians today who can generate massive attention—and controversy—simply by being himself. The performance is a testament to the power of unfiltered comedy in the modern media landscape.