Jimmy Kimmel and Ryan Reynolds
On July 24, 2024, viewers tuning in to Jimmy Kimmel Live! didn’t find Jimmy Kimmel behind the desk. Instead, they found Deadpool and Wolverine. Ryan Reynolds and Hugh Jackman took over as guest hosts the night before Deadpool & Wolverine hit theaters, singing the Golden Girls theme song and joking about embarrassing prosthetics.
It was one of many fun moments between Jimmy Kimmel and Ryan Reynolds. Reynolds has been a regular guest on Kimmel’s show for years, and their shared love of sarcastic humor makes them a natural fit.
This article covers their best moments together, both of their backgrounds, career highlights, and where they are in 2026.
Quick Facts
| Jimmy Kimmel | Ryan Reynolds | |
|---|---|---|
| Full name | James Christian Kimmel | Ryan Rodney Reynolds |
| Born | November 13, 1967 | October 23, 1976 |
| Birthplace | Brooklyn, New York | Vancouver, British Columbia, Canada |
| Known for | Jimmy Kimmel Live!, Oscars host | Deadpool, Mint Mobile, Wrexham AFC |
| Spouse | Molly McNearney | Blake Lively |
| Business | Kimmelot production company | Maximum Effort, Aviation Gin, Mint Mobile, Wrexham AFC |
Best Moments: Jimmy Kimmel and Ryan Reynolds
The 2021 Talk Show Swap
In November 2021, Reynolds was scheduled to appear on Jimmy Kimmel Live!, while Will Ferrell was booked on The Tonight Show Starring Jimmy Fallon. At the last minute, the two actors swapped. Reynolds showed up on Fallon’s show and Ferrell showed up on Kimmel’s, each in street clothes and doing impressions of the other. Reynolds joked that it was easier to “help a friend out” since Ferrell lived in Los Angeles. Fans loved the surprise.
Guest Hosting With Hugh Jackman (2024)
On July 24, 2024, Reynolds and Hugh Jackman guest hosted Jimmy Kimmel Live! to celebrate Deadpool & Wolverine. They talked about the film’s original title, why Jackman returned as Wolverine, and the infamous Wolverine popcorn bucket. Emma Corrin joined as a guest, and the show featured a clip of Peggy, the dog who plays “Dogpool.” The two stars also sang the Golden Girls theme song, a nod to their real-life friendship.
Regular Appearances
Over the years, Reynolds has visited Kimmel many times to promote films like Deadpool, Free Guy, and The Adam Project. His dry, self-mocking humor fits Kimmel’s style, and their interviews often turn into joke battles.
Jimmy Kimmel: Early Life and Education
Jimmy Kimmel was born on November 13, 1967, in Brooklyn, New York, and moved to Las Vegas at age nine. He attended UNLV and Arizona State University but didn’t graduate. He spent years in radio, including on KROQ in Los Angeles.
Career Timeline
- 1997: Co-hosted Win Ben Stein’s Money, winning a Daytime Emmy.
- 1999: Co-created The Man Show with Adam Carolla.
- 2003: Launched Jimmy Kimmel Live! on ABC.
- 2017, 2018, 2023, 2024: Hosted the Academy Awards.
- 2025: His show was briefly pulled off the air in September after comments about Charlie Kirk’s killing, then returned about a week later. In December, he extended his contract through May 2027.
- 2026: ABC denied a September report that the show would end in 2027.
Ryan Reynolds: Early Life and Education
Ryan Reynolds was born on October 23, 1976, in Vancouver, British Columbia, the youngest of four brothers. His father was a food wholesaler and his mother worked in retail. He started acting as a teen on the Canadian series Hillside, known in the US as Fifteen. He briefly attended Kwantlen Polytechnic University before focusing on acting full-time.
Career Timeline
- 1998 to 2001: Starred in the ABC sitcom Two Guys, a Girl and a Pizza Place.
- 2002: Led the comedy National Lampoon’s Van Wilder.
- 2009: Starred in The Proposal with Sandra Bullock, a box office hit.
- 2012: Married Blake Lively. They have four children.
- 2016: Starred in Deadpool, which became one of the highest-grossing R-rated films ever.
- 2018: Released Deadpool 2. Bought a stake in Aviation Gin, which was later sold to Diageo.
- 2020: Mint Mobile, which he co-owned, grew quickly with his comedic ads. T-Mobile later bought the company in a deal announced in 2023.
- 2021: Co-bought Wrexham AFC with Rob McElhenney, documented in the series Welcome to Wrexham.
- 2024: Deadpool & Wolverine became the highest-grossing R-rated film of all time.
How Their Careers Compare
| Category | Jimmy Kimmel | Ryan Reynolds |
|---|---|---|
| Industry | Late-night TV, comedy | Film, advertising, sports |
| Breakout | Win Ben Stein’s Money | Van Wilder, then Deadpool |
| Biggest platform | Jimmy Kimmel Live! | Deadpool films |
| Business ventures | Production company | Gin, phone service, soccer club, ad agency |
| Comedy style | Sharp, satirical | Dry, self-deprecating |
| Canadian link | None | Vancouver native |
Why They Work So Well Together
Jimmy Kimmel and Ryan Reynolds share a similar sense of humor. Both love sarcasm, pranks, and poking fun at themselves. Kimmel’s show often features playful feuds, like his long-running fake rivalry with Matt Damon. Reynolds has his own famous fake feud with Hugh Jackman. Put them together, and the jokes write themselves.
Reynolds’ ad agency, Maximum Effort, also built its reputation on quick, funny marketing videos, the same kind of fast humor that drives late-night comedy.
What They Have in Common
- Comedy first: Both are known for humor, even in serious moments.
- Business savvy: Kimmel runs a production company. Reynolds built and sold successful brands.
- Strong families: Kimmel has four children. Reynolds and Lively have four children.
- Fake feuds: Kimmel with Matt Damon, Reynolds with Hugh Jackman.
- Award show hosting: Kimmel has hosted the Oscars four times, and Reynolds has presented at major award shows.
Where Are They Now?
Jimmy Kimmel continues to host Jimmy Kimmel Live! under a contract through May 2027.
Ryan Reynolds continues to act, produce, and run his businesses. Wrexham AFC’s rise through the English leagues, documented in Welcome to Wrexham, keeps him in the headlines on both sides of the Atlantic.
Where to Watch
Clips of the 2021 swap and the 2024 guest hosting episode are on the official Jimmy Kimmel Live! YouTube channel. The full guest hosting episode is also available on Hulu. Welcome to Wrexham streams on FX and Hulu.
Fake Feuds: Matt Damon and Hugh Jackman
One thing Jimmy Kimmel and Ryan Reynolds share is a love of fake feuds.
Kimmel’s running gag with Matt Damon began in the mid-2000s, when he ended a show by saying, “Apologies to Matt Damon, we ran out of time.” The joke grew into years of pranks, surprise appearances, and Damon “taking over” the show. It even spilled onto the Oscars stage when Kimmel hosted.
Reynolds has a similar bit with Hugh Jackman. For years, the two traded insults online and in ads, with Reynolds mocking Jackman’s singing and Jackman poking fun at Reynolds’ films. The feud turned into a real-life partnership when Jackman returned as Wolverine opposite Reynolds’ Deadpool.
That’s why the July 2024 guest hosting night felt so fitting. Two men with a famous fake feud took over the show of a host known for his own. For fans of Jimmy Kimmel and Ryan Reynolds, it was a perfect blend of running jokes and real friendship. It’s a good example of how Jimmy Kimmel and Ryan Reynolds use humor to keep fans entertained between projects.
In Short
In short, Kimmel built a late-night institution, while Reynolds built a movie career and a business empire on top of it. Both rely on the same tool: quick, self-aware humor that makes audiences feel like they’re in on the joke.
Final Thoughts
Jimmy Kimmel and Ryan Reynolds have built one of late-night’s most entertaining partnerships. From the surprise 2021 swap with Will Ferrell to the night Deadpool and Wolverine took over the show, their moments together keep fans laughing. Beyond the jokes, both have built huge careers and businesses through humor and hard work. For fans of either star, the Jimmy Kimmel and Ryan Reynolds story is a perfect example of comedy chemistry.
Key Takeaways
- Jimmy Kimmel was born November 13, 1967, in Brooklyn. Ryan Reynolds was born October 23, 1976, in Vancouver.
- In November 2021, Reynolds and Will Ferrell swapped talk show appearances at the last minute, with Ferrell visiting Kimmel and Reynolds visiting Fallon.
- On July 24, 2024, Reynolds and Hugh Jackman guest hosted Jimmy Kimmel Live! the night before Deadpool & Wolverine opened.
- Kimmel launched Jimmy Kimmel Live! in 2003, has hosted the Oscars four times, and is under contract through May 2027.
- Reynolds rose with Van Wilder and Deadpool. Deadpool & Wolverine became the highest-grossing R-rated film ever in 2024.
- Reynolds built and sold stakes in Aviation Gin and Mint Mobile and co-owns Wrexham AFC with Rob McElhenney.
- Jimmy Kimmel and Ryan Reynolds share a love of sarcastic humor, fake feuds, and self-mocking comedy.
