Top 10 Hilarious Jimmy Kimmel Guests

It rarely gets funnier than Dave Chappelle. This famed comic rose to popularity through his early standup performances – namely the 2000 HBO special “Killin’ Them Softly” – but later shot to superstardom with the debut of Comedy Central’s “Chappelle’s Show” only to shock the world by taking a sudden and lengthy personal break from showbiz. Thankfully, Dave’s back with new stand-up specials on Netflix, and no one seems happier with his return than Jimmy Kimmel. In true Chappelle fashion, the comedian tells it like it is during this segment with the TV host, mixing jokes with biting honesty, leaving both the audience and Kimmel himself in stitches. But, make no mistake, he’s not interested in reviving his past fame; he really just needed a paycheck.

Anyone that grew up on “Friends” knows that Aniston has killer comedic chops, and she hasn’t stopped being funny in the years since, appearing in numerous hit comedies like 2013’s “We’re the Millers” and teamed up with long-time pal Adam Sander for the Netflix comedy “Murder Mystery” in 2019. She remains a sex symbol in the eyes of many, and Jimmy knows it, writing some not so subtle “Friends” fan fiction with himself as Ross trying to get Aniston into bed. Backed by fellow “Friends” co-stars Courteney Cox and Lisa Kudrow, though, Aniston cuts Jimmy’s dream threesome short and politely suggests he should go F himself instead.

He’s everyone’s favorite stoner, and it kind of feels like we’ve watched him grow up onscreen since his debut in high-school cult comedy series “Freaks and Geeks.” Seriously, it seems as if Rogen featured in many of the biggest and most memorable funny movie of the aughts: starting with “The 40 Year Old Virgin,” and “Knocked Up” before moving on to “Superbad;” (which he also-co-wrote) and “Pineapple Express”. The dude is no stranger to laughs, and so when he sat down with Jimmy to talk about his “Hilarity for Charity” stand-up special in 2018, he proved that he’s still got it, leaving Jimmy and the audience in stitches talking about his favorite people to smoke weed with. Spoiler: Snoop Dogg is, ahem, high on the list…

He’s not only one of the most popular U.S. Presidents in 21st century memory, but – if he had failed to ever run for office – he could have had a bright future in comedy as well. The man’s just got good timing! He’s roasted Zach Galifianakis on his own show “Between Two Ferns;” he famously dropped the mic during his last White House Correspondents dinner; and he even slow jammed the news with other popular late night host Jimmy Fallon. So, it just makes sense that he’d also appear on Kimmel’s show in one of its most popular bits: Mean Tweets. Our favorite tweet? Obviously, it’s the dude busting Obama’s chops for the rising price of Coors Light at corner stores.

Sure, we associate ScarJo more with her dramatic roles and her appearances as Black Widow in the Avengers movies, but she’s not a total stranger to comedy – after all she did appear (briefly) in “Home Alone 3.” Annyyyywayyy… we think ScarJo’s humor in the MCU is just scratching the surface, and she shows us as much in this interview, claiming that Kimmel keeps her body toned year round with his home exercise routine, “Hottie Body Hump Club”. Yes, it’s just a bunch of sexy starlets humping exercise balls with Jimmy cheering them on, but Johansson clearly enjoys the chance to embrace her silly side for a change -hamming it up big time in front of the cameras. It’s just so perfectly absurd!

It would be pretty hard to put together a list of funny people and not have Jim Carrey on it. He’s been responsible for busting many a gut since his days on the underrated sketch comedy show “In Living Color” in the early ‘90s, and he brought to life such memorable characters as Ace Ventura, Lloyd from “Dumb and Dumber” and the morose Cable Guy. Although he’s not as active in movies and comedy as he once was, Jim still found time to grace Jimmy’s guest chair in 2017 and give us all a few laughs when he joked about the irony of growing a massive, grizzly-man beard while continually shaving his… ummm… southern regions.

Singer/actress? Check. Businesswoman? Check. Fashion designer? Yup, she does that too! Comedian?? Surprisingly, yes! It turns out RiRi has a silly streak of her own and loves a good laugh, particularly when watching Jimmy’s April Fools Day Pranks. So, when she appeared on the show back in 2015 on (you guessed it…) April Fools Day, she sure as hell wasn’t going to let the opportunity to prank Jimmy slip by. It’s probably a lot of guys’ fantasies to wake up to Rihanna dancing and throwing money at them, but – from the looks of it – Jimmy’s not one of them.

Better known for his more dramatic roles, Damon definitely revels in the opportunity to get silly off-screen. Sure, the “Oceans” movies had comedic elements, and he’s appeared on TV comedies such as “30 Rock” and “Entourage,” but he’s still best known for being funny outside of roles... like his appearance on “Jimmy Kimmel Live.” The hilarious feud between Jimmy and Matt goes back a long way and has seen highlights such as “I’m F*cking Matt Damon,” Matt’s takeover of Jimmy’s show, and Jimmy writing mean tweets for Damon to read. To top off all this craziness, Matt’s buddy Ben Affleck got involved too, but in support of Jimmy! Cue the comedic comeback known as “I’m F*cking Ben Affleck.”

Yes, we all know him as Jim from “The Office,” and we came to love his character as he endlessly pranked Dwight, but it turns out he’s pretty good at pranks in real life too – especially those aimed at former neighbor Jimmy Kimmel. John and Jimmy’s prank feud goes back to 2011 when John placed some cute, innocent Christmas decorations in Jimmy’s house and it all escalated from there. John’s been drowned in eggnog, Jimmy’s had his car covered in wrapping paper, and, in this 2018 appearance on the show, John got some sweet revenge by advertising where Jimmy was staying in Brooklyn while his show was on location in New York. We wonder if Jimmy ended up getting any uninvited guests??

Before we unveil our top pick, here are a few honorable mentions:

Chris Rock

Larry David

Ricky Gervais

Joseph Gordon-Levitt

Charles Barkley

Sometimes it can be hard to tell where cocky, brash and hilarious Tony Stark begins and where Robert Downey Jr. ends. Because, well, RDJ is all those things as well! His interviews are the stuff of legend, his Instagram account is outrageous, and he’s constantly cracking up his co-stars with his off-the-wall personality. Also, you just never know what he’ll say in public, like when Kimmel questioned how Downey Jr. got Chris Evans to take the Captain America role, and RDJ joked that he’s basically responsible for the MCU existing. He’s clearly speaking in jest, but we all know that every joke is 50% truth, and RDJ does cocky humor to perfection.