24 of the Silliest, Sweetest“ Late Show with” “Stephen Colbert” Moments That Show How Much We'll Miss the Show
24 of the Silliest, Sweetest“ Late Show with” “Stephen Colbert” Moments That Show How Much We'll Miss the Show
Stephanie SengweThu, May 21, 2026 at 10:15 PM UTC
0
Stephen Colbert and Michael Keaton
Credit: Scott Kowalchyk/CBS via Getty
Stephen Colbert can turn even the biggest A-lister into a goofball.
Over the course of his 11-year tenure hosting The Late Show with Stephen Colbert, the comedian had some of the world's biggest stars participating in some silly and fun antics. Though you may not be surprised to find out that actors such as Will Ferrell and Aubrey Plaza always come ready to play, he also got Barack Obama to compete in a game of wastepaper basketball, Kate Winslet to recreate that infamous Titanic endingand Michael Keaton to dress up as a pigeon, which proves that when it came to late night antics, he reigned supreme.
As The Late Show airs its final episode on CBS tonight at 11:35 p.m. ET, look back at some of the silliest, most fun and whimsical moments from the show over the years.
Related: Stephen Colbert Reveals What He'll Do the Day After The Late Show Ends (Hint: It Involves Getting 'Drunk') (Exclusive)
01 of 24
Walk Like a King
Jonathan Groff and Stephen Colbert
Credit: Jeffrey R. Staab/CBS via Getty
Back in 2015, Colbert got a full tutorial on how to walk like a king from Hamilton star Jonathan Groff — posture-enhancing books and all.
02 of 24
Getting Cozy
Stephen Colbert with Michelle Obama
Credit: Scott Kowalchyk/CBS via Getty
Colbert surprised the audience in 2016 by getting former first lady Michelle Obama to act in his "Blanket Fort" skit.
03 of 24
Will Ferrell's New Endeavor
Will Ferrell and Stephen Colbert
Credit: Heather Wines/CBS via Getty
In 2016, Will Ferrell felt like trying his hand at being an exotic animal expert, and since The Late Show had hadn't had one on yet, he decided to "step in and fill the gap." The actor brought a "short-spine Peruvian mongoose," a "Mongolian bush tiger," and the above pictured "rare duck-bodied platypus," named Cilantro.
04 of 24
Losing Their Cool
Margot Robbie, Tina Fey and Stephen Colbert
Credit: Heather Wines/CBS via Getty
Colbert, along with Tina Fey and her Whisky Tango Foxtrot costar, Margot Robbie, couldn't hold in their laughter after Robbie detailed that she had taken up a new hobby as a tattoo artist, but then misspelled a word while tattooing a colleague from Suicide Squad.
05 of 24
Hurray for Carol!
tephen Colbert and Carol Burnett
Credit: Scott Kowalchyk/CBS via Getty
Carol Burnett may have admitted to having been a bit of a con artist in her early days while on the show in 2017, but clearly Colbert (and all of us, really) only love her more for it.
06 of 24
Turning Tables
Stephen Colbert with Kerry Washington
Credit: Scott Kowalchyk/CBS via Getty
Colbert got Oliva Pope-d into the hot seat when Kerry Washington visited in 2018.
07 of 24
Right at Home
Jennifer Lawrence and Stephen Colbert
Credit: Scott Kowalchyk/CBS via Getty
Colbert indulged the ever-playful Jennifer Lawrence as she took her shoes off and and got comfortable when she visited in 2018.
08 of 24
Come and Claim Him
Stephen Colbert with Liv Tyler
Credit: Scott Kowalchyk/CBS via Getty
Colbert geeked out when Liv Tyler brought her Lord of the Rings sword during her appearance in 2018. A huge fan of the film franchise, the comedian then asked Tyler to "indulge in a fantasy of mine" and he played Frodo as they recreated the classic, "Give Up the Halfling" scene from The Fellowship of the Ring.
09 of 24
Singing with the Best
Stephen Colbert with Jennifer Hudson
Credit: Scott Kowalchyk/CBS via Getty
Not many are able to compare when Jennifer Hudson starts singing, but the comedian held his own as they performed an impromptu duet of "Oh Holy Night" in 2019.
10 of 24
A Christmas Witch
Aubrey Plaza and Stephen Colbert
Credit: Scott Kowalchyk/CBS via Getty
In 2021, friend of the show Aubrey Plaza came dressed as the main character in her book, The Legend of the Christmas Witch. Colbert interviewed the actress as if nothing was amiss.
11 of 24
A Tragically Good Time
Stephen Colbert with Denzel Washington
Credit: Scott Kowalchyk/CBS via Getty
The talk show host perfectly matched Denzel Washington's vibes as the Oscar-winning actor stopped by to promote The Tragedy of Macbeth in 2021.
Advertisement
12 of 24
Men's Bestfriend
Stephen Colber with Andy Cohen and Anderson Cooper
Credit: Scott Kowalchyk/CBS via Getty
Things got super cute as Colbert, Andy Cohen and Anderson Cooper told tiny little lies about some tiny little puppies in an effort to help them get adopted during the 2022 holiday season.
13 of 24
Hooping with the President
Barack Obama and Stephen Colbert
Credit: CBS via Getty
Ever competitive, Colbert challenged former President Barack Obama to a game of wastepaper basketball in 2020. The talk show host won the face-off, but questions remained about whether or not he had cheated.
14 of 24
Ta-Dah!
Stephen Colbert with Emily Blunt
Credit: Scott Kowalchyk/CBS via Getty
Colbert made Emily Blunt feel every bit the "resplendent snow queen" he dubbed her when she came on in 2022.
15 of 24
Asking the Tough Questions
Scarlett Johansson and Stephen Colbert
Credit: Scott Kowalchyk/CBS via Getty
Colbert was gobsmacked when Scarlett Johansson, like Joaquin Phoenix previously, couldn't decide which she preferred, apples or oranges, during the "Colbert Questionert." Johansson, for her part, was tickled by his despair.
16 of 24
Birdmen
Stephen Colbert and Michael Keaton
Credit: Scott Kowalchyk/CBS via Getty
Michael Keaton is often said to be as one of the best actors to play Batman. For his May 18 appearance, however, Colbert got him to call back to another avian-related movie of his by getting the Birdman actor to dress up as a pigeon for a skit.
17 of 24
The Great Debate
Stephen Colbert and Kate Winslet
Credit: Scott Kowalchyk/CBS via Getty
Could Jack have fit on the door with Rose in Titanic? Kate Winslet certainly thought so. Colbert helped the actress "fix the ending" by playing Jack and reenacting a scenario in which he also hopped up on the door.
18 of 24
Joyous Occasion
Stephen Colbert with Taylor Swift
Credit: Scott Kowalchyk/CBS via Getty
A newly engaged Taylor Swift stopped by last December and spoke about all things engagement, wedding planning and the fact that even though she is global superstar, she has no desire to have a recording studio in her home.
19 of 24
Reliving Moments
Stephen Colbert with Jamie Lee Curtis
Credit: Scott Kowalchyk/CBS via Getty
Things got chaotic pretty fast when Jamie Lee Curtis visited The Late Show while promoting Freakier Friday last summer and told a story about how much Colbert is obsessed with her husband, Christopher Guest.
20 of 24
Strike Force Five
Stephen Colbert and guests Jimmy Kimmel, Jimmy Fallon, John Oliver, and Seth Meyers
Credit: Scott Kowalchyk/CBS News via Getty
Colbert and the Strike Force Five gang — Jimmy Fallon, Seth Meyers, John Oliver and Jimmy Kimmel — reunited for an episode on May 11 and struck a Rockettes-esque pose as they bowed out.
21 of 24
Forever Laughing
Stephen Colbert and Evie Colbert
Credit: Scott Kowalchyk/CBS via Getty
Stephen shared a good laugh with wife Evie as they read through some silly Mother's Day cards when she visited earlier this month.
22 of 24
Wind Beneath My Wings
Stephen Colbert and John Krasinski
Credit: Scott Kowalchyk/CBS via Getty
John Krasinski was thrilled to see his host when he stopped by on May 7. And if you think this Dirty Dancing-esque lift was is wild, take a look at this leg wrestling match the two men partook in.
23 of 24
Asking the Big Questions
Stephen Colbert and guest Julia Louis-Dreyfus
Credit: Scott Kowalchyk/CBS via Getty
"What is the difference between living and being alive?" "Is violence ever the answer?" "Where will Stephen be in five years?" Are just some of the big questions Colbert and Julia Louis-Dreyfus tackled when she appeared on the show on May 12. And FYI, violence is never the answer, per Dreyfus. It's simply, "too many letters for the Wordle."
24 of 24
End of an Era
Stephen Colbert with David Letterman
Credit: Scott Kowalchyk/CBS via Getty
On May 14, Colbert got a visit from former Late Show host David Letterman. The legendary hosts shared a laugh while hanging out on the rooftop of the Ed Sullivan building and partaking in the "Wanton Destruction of CBS Property" during which they may or may not have tossed some stuff off the building.
on People
Source: “AOL Entertainment”
