Hollywood is a harsh town. In order to survive, you need to have thick skin. Otherwise, you’ll be devoured and discarded like you were yesterday’s trash.
The most successful and long-lasting celebrities, not only understand this fact — they embrace. So for the sake of having fun, let’s check out a bunch of times that celebrities made fun of each other!
1. Matt Damon and Sarah Silverman’s duet for Jimmy Kimmel.
You may have forgotten but Sarah Silverman and Jimmy Kimmel used to date. Shortly after they called it quits, Sarah appeared on Jimmy Kimmel Live , to unveil a new project she’d been working on.
The song was called “I’m [expletive]-ing Matt Damon.”
2. The time Snoop Dogg trolled every single mumble rap artist out there.
In one fell swoop, Snoop Dogg threw shade at every single mumble-rapper out there. He flatly stated that the problem with Hip Hop today is that all the artists sound the same.
Future, the Migos, even Young Thug!
3. Rihanna turned the tables on Jimmy Kimmel.
As an April Fool’s prank, the pop star, with the help of Jimmy’s wife, broke into his bedroom at 1 o’clock in the morning.
She exploded cannons of confetti while she performed her song “[expletive] Better Have My Money” to an extremely confused and out-of-it Kimmel.
4. When Ellen DeGeneres secretly taped Portia De Rossi doing her Jane Fonda workout.
Portia agreed to allow Ellen to sit in on her workout. She did not, however, sign up to have the video plastered all over social media.
But in the end, it was Portia who would have the last laugh.
Portia responded by uploading Ellen on the treadmill.
The daytime talk show host is hammering hard on the treadmill. She also appears to be a fan of Bruno Mars.
Listen and you can hear Ellen belting out “Uptown Funk” at the top of her lungs.
5. When Ryan Reynolds posted this hilarious birthday collage for Blake Lively.
These are incredible photos of Ryan, but sadly the same cannot be said for Blake. Clearly, these two are madly in love.
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If I ever tried to post such a ‘candid’ shot of my partner, I’d be sleeping in my car.
6. The time Jake Gyllenhaal got Ryan Reynolds to show up to a party wearing an ugly Christmas sweater.
According to the comment on Ryan’s Instagram, both Jake and Hugh had told him that they were going to an Ugly Christmas Sweater Party.
Can you imagine how embarrassed you’d feel showing up to a party with a giant bow pinned to your chest?
7. The time Chris Pratt and Jennifer Lawrence played a game of Playground Insults.
I think it’s pretty clear to see that Chris wasn’t looking to play hardball. His co-star, on the other hand, was out for blood!
This may be the best pairing in the entire Playground Insults series.
8. When Chrissy Teigen called out John Legend’s lack of baseball knowledge on IG.
Chrissy’s comment reads “I’m dying. No one in the world knows less about baseball than these two @mrmikerosenthal @johnlegend @jenatkinhair.”
I would’ve personally chosen to attack John on his choice of team, but that’s probably because I’m a Jays fan.
9. The time Martha Stewart slayed at the *Roast of Justin Bieber*.
I think many people were confused at first when they saw Martha’s name attached to the dais. It certainly didn’t last long, because less than a minute into her monologue Martha had the entire audience roaring with laughter.
10. When Will Ferrell interviewed George W. Bush — as George W. Bush.
Of all the great comedic roles that Will Ferrell has undertaken over the course of his career, my favorite is former President George W. Bush.
This satirical mockumentary-style interview showcases Will at the very top of his game.
11. Ricky Gervais’ opening monologue at the 2019 Emmy Awards.
Holy smokes! Ricky Gervais certainly took no prisoners during his most recent stint as host of the Emmys.
My favorite part was when he accused the entire room of having less collective education than Greta Thunberg .
12. Hugh Jackman’s commercial for Aviation Gin.
The ongoing feud between Hugh Jackman and Ryan Reynolds is legendary. But the apex moment came when the pair decided to make commercials for each other’s respective businesses.
Watching Hugh pour Ryan’s gin on the floor with a straight face had me howling.
13. “I’m Rick James, [expletive]” from *Chapelle’s Show*.
Be honest: has there ever been a more hilarious celebrity sketch than Dave Chapelle’s iconic Rick James ? No, there hasn’t been.
No matter how many years go by, this is and always will be funny.
14. When Kevin Hart made fun of everybody at the 2013 NBA All-Star Game.
Kevin Hart is the roast master. I could have written a list totally dedicated to Kevin Hart making fun of various celebs in Hollywood.
But of all the people Kevin has trolled, no one has ever got it as bad as Shaq and Charles Barkley.
