2020–present: Career expansion
In December 2020, Gillis and comedian John McKeever launched the web series Gilly and Keeves, featuring comedy sketches starring Gillis and McKeever such as "ISIS Toyota", "Uncle Daycare", and "Trump Speed Dating". On September 7, 2021, Gillis released his first live comedy special, Shane Gillis: Live in Austin on YouTube. Comedy website The Laugh Button ranked Gillis's special in second place in their top 20 comedy specials of 2021. Since 2021, Gillis has made a series of appearances on Joe Rogan's podcast The Joe Rogan Experience alongside comics Mark Normand and Ari Shaffir, known as the "Protect Our Parks" episodes. Gillis released his second live comedy special, Shane Gillis: Beautiful Dogs on September 5, 2023, on Netflix. Since 2018, Shane Gillis has been a regular part of the annual comedy festival Skankfest.
In 2023, Gillis had a recurring role on the Peacock series Bupkis, starring Pete Davidson. In 2024, Gillis hosted the February 24 episode of Saturday Night Live (season 49, episode 12), nearly four and a half years after his firing from the show in September 2019. Gillis' hosting received mixed reviews.
In February 2024, Gillis struck a deal with Netflix for a scripted workplace comedy as well as his second special with the streamer. Gillis would serve as an executive producer, a writer and co-creator of the show Tires based on his pilot on YouTube. The six-episode series premiered on May 23 on the service. Tires was renewed for a second season on May 21, 2024. In 2024, Gillis also appeared in the music video for Eminem's new single "Houdini."
In October 2024, during a comedy festival entitled Skankfest in Las Vegas, Gillis stated that he declined an offer to impersonate Donald Trump for the entire 50th season of SNL to attend "Coke Magic", one of the shows at the festival.
Gillis appears in the movie Easy's Waltz, in a supporting role that was originally written for comedian Norm Macdonald, who died before the film began production.
In February 2025, Gillis appeared in an advertisement for Bud Light titled "Big Men on Cul-De-Sac," which aired during Super Bowl LIX. He appeared in the advertisement with Peyton Manning and Post Malone. This ad was seen as an attempt by Anheuser-Busch to win back its traditionally masculine audience after the 2023 Bud Light boycott, although it received a mixed reception from ad critics.
In March 2025, Gillis was added as a playable character to the video game EA Sports College Football 25's Ultimate Team mode, as a 98-rated middle linebacker for the Notre Dame Fighting Irish, as part of the 'Names of the Game' promotional event.
On July 16, Gillis hosted ESPN's 2025 ESPY Awards.
In May 2026, Gillis hosted The Roast of Kevin Hart in Los Angeles and produced by Netflix.
On July 17, 2026, Gillis broke the Guinness World Record for the largest audience for a comedian with 73,946 attending his comedy show at Lincoln Financial Field in Philadelphia. This sold-out show also broke the record for the most tickets sold to a solo comedy show, selling 76,212 tickets.
On October 10, 2026, Gillis hosted Saturday Night Live for a third time. His monologue, in which he said women who go to the gym "just dress like whores now", was criticized for being sexist. Several comedians criticized him, including Dan Levy, who labeled his comments as "misogynist", adding that "the more men speak about women this way in the media, the more men will treat them like 'objects'." Others who criticized Gillis included former SNL cast members Cecily Strong and Ego Nwodim, as well as Kathy Griffin, Jessica Valenti and Jenna Bush Hager. Tony Maglio of The Hollywood Reporter wrote, "It wasn't just the wrong place for the joke — it was decidedly the wrong time" in reference to the 2024 Cornell University rape allegations in the headlines. Ania Magliano, on the October 17 episode of Saturday Night Live UK, referenced and criticized both the monologue's content and Gillis himself.
