Top 20 Hilarious Stephen Colbert Moments

#20: Teaming Up with Jon Stewart & John Oliver

“Night of Too Many Stars” (2017)

While hosting this charity event, Jon Stewart couldn’t do it alone. He utilizes multiple actors, comedians, and performers to make his monologue shine. This segment parodies shows like “America’s Got Talent” and the curse of the red buzzer. Stephen Colbert interjects early on, critiquing his old boss’ performance and jokes. This is already funny before John Oliver even shows up. There’s more than a few self-referential lines at the trio’s expense, culminating in a shouting match. Stewart finally steps in to stop his former employees from hurting each other. If you’re a fan of any one of these three, you’ll love seeing them interact and joking around again.

#19: LOTR Rap

“The Late Show with Stephen Colbert” (2015-)

Most fans of Stephen Colbert know that he’s a massive Tolkien fan. Unable to pass up a good opportunity, the comedian did a hip-hop tribute to “The Lord of the Rings” films for their anniversary. This includes more than a few cameos from cast members and even Anna Kendrick. If you’re not laughing at this crazy song, you’ll be entertained by the frequent surprises. Method Man and Killer Mike also make appearances along with a few other actors. Colbert pulls out all the stops here as he embraces his rap alter ego. Along with some silly lyrics and references, the host makes a case for why these movies could be the best trilogy ever.

#18: Bruce Willis vs. Stephen Colbert

“The Late Show with Stephen Colbert” (2015-)

Known for his action movie roles, Bruce Willis is a much tougher guy than Stephen Colbert. This all changes when the “Late Show” host asks about the actor doing his own stunts. The “Die Hard” star takes offense to Colbert’s claims, with the two deciding to duke it out. This leads to a choreographed fight full of thrills, spills, and over-the-top mayhem. Two other performers take over, making each maneuver look even more impressive. There’s even some clever surprises here like a drum set and a guitar. After a high fall, Willis finally admits that he’s been lying after all. The last moment makes it all worthwhile as a table dive seals the deal.

#17: Nicki Minaj’s Colbert Rap

“The Late Show with Stephen Colbert” (2015-)

With this rap star on the show, Stephen Colbert couldn’t help but dive into her catalog. One question involves the celebrity men that Nicki Minaj mentions in her music. The host lets curiosity get the best of him, asking to be included on a list of famous guys. Minaj is quick to offer up a freestyle that embarrasses Colbert. The audience and even the band celebrate the moment, with the presenter hiding behind his notecards. Kudos to the guest for being so fast and leaving the door open for this surprise. While the comedian is the farthest thing from a hip-hop icon, this is the closest he might come to the title. At the very least, the improvised verse and reaction is laugh-out-loud funny.

#16: “Not Yet”

“The 37th Annual Kennedy Center Honors” (2014)

Back in 2014, Stephen Colbert prepared to leave his show at Comedy Central. He then became the heir to the “Late Show” on CBS. This prompted one of the funnier moments at the Kennedy Center Honors. With David Letterman presenting, Colbert decided to follow his predecessor onstage and stand next to him. It looked like Letterman might be replaced yet again by the younger comedian. With the audience in stitches, the elder presenter only needed to say one thing to make people happy. The “Colbert Report” host ended up getting laughs without needing any dialogue at all.

#15: Islam vs. Christianity

“The Daily Show” (1996-)

For the “Even Stevphen” segment on “The Daily Show,” Stephen Colbert and Steve Carell face-off in a religious battle. They have a playful discussion about both belief systems while making themselves the butt of the joke. Colbert especially digs into Christianity, making funny asides about the line between faith and biblical literalism. Carell plays along while serving up some awesome rebuttals. Even if you’re Muslim or Christian, you can still find plenty to chuckle about here. The clip also reminds you of how great these two were before they became superstars. Both quick-witted and excellent performers, this duo prove that they’re great friends and an amazing comedy team.

#14: Prince Charles Report

“The Daily Show” (1996-)

In the 2000s, Prince Charles faced a rumor about an alleged relationship with a valet. “The Daily Show” tackles the subject with the exact amount of hilarity you’d expect. Correspondent Stephen Colbert wants to talk more about the allegations, but he’s cautious about crossing any legal lines. This leads him to use some funny double entendres and even bring out a prop. Colbert’s choices with a banana are unforgettable and hilarious, with even Stewart breaking at the sight of everything. The “Late Show” presenter isn’t afraid to go boldly into raunchy territory with reckless abandon.

#13: Fighting Conan O’Brien & Jon Stewart

“Late Night with Conan O’Brien” (1993-2009)

Back during a writer’s strike in 2008, late night hosts needed a way to keep their shows going without a script. This led Stephen Colbert to throw down with Jon Stewart and Conan O’Brien in a comedic rivalry. With a goofy disagreement over Mike Huckabee, the trio of hosts ended up meeting on O’Brien’s show to have a dramatic battle. The comedians then went into the hallway to start an all-out brawl. This included some fun nods to pro-wrestling, with some entertaining stunts for added measure. It’s especially funny to watch these men pretend to fall down stairs.

#12: “Friday” Cover

“Late Night with Jimmy Fallon” (2009-14)

Almost anyone that remembers the early 2010s knows this tune. Rebecca Black’s song inspired all kinds of tributes, critiques, and parodies. Stephen Colbert did his own version of “Friday” with some help from the “Late Night with Jimmy Fallon” staff. Fallon introduced “The Colbert Report” host, with the latter getting some backup from The Roots and “American Idol” winner Taylor Hicks. The cover goes from a moody introduction to a triumphant chorus. Even if you find the original annoying, this one reminds you that it’s okay to enjoy a guilty pleasure. It’s all delivered with the kind of comedic energy that’ll have you laughing or singing along. There’s even some dancers to bring it all home.

#11: The Word: Truthiness

“The Colbert Report” (2005-14)

At his peak, Stephen Colbert’s character on “The Colbert Report” stood for his own kind of “truth.” This particular segment highlights this core attitude. The host leans towards his own gut instincts, telling viewers to not lean on any reference materials. It’s a hilarious way to promote less reading and more ignorance. Favoring feeling over brain power, the comedian mentions one controversial Supreme Court nomination from George W. Bush. The on-screen bumpers only give the audience more reason to think and laugh. With “The Word” being one of his most consistent bits, the presenter once again nailed the bravado of an opinionated pundit.

#10: Getting Daft Punk’d

“The Colbert Report” (2005-14)

While he likely didn’t feel lucky at first, Colbert managed to turn a decision by Comedy Central’s corporate parent Viacom to cancel an appearance by Daft Punk on The Colbert Report into comedy gold. After explaining how he’d only just found out the day before that another Viacom subsidiary MTV had exclusive performance rights to the French duo, he started dancing to Daft Punk’s hit Get Lucky. Various celebrities joined him in an original music video, most notably Breaking Bad star Bryan Cranston on rollerskates in what looked like a disco. When life gives you lemons, you make a funny video.

#9: Only in Monroe

“Only in Monroe” (2015)

Stephen Colbert can host anything well. He proved it when, during the break between the Colbert Report and The Late Show, he took over hosting duties for one episode of a local Monroe, Michigan public access show “Only in Monroe”. He interviewed the show’s regular hosts and brought up a very local and impressively out of date Yelp review before introducing his special guest, Michigan native Eminem, whom Colbert referred to by his given name Marshall Mathers. After pretending not to know his guest was famous, the pair co-presented the ultimate local show segment, a real Monroe, Michigan Community Calendar.

#8: Crude Political Drawings

“The Late Show with Stephen Colbert” (2015-)

Colbert’s political comedy can be witty highbrow satire, but sometimes downright crude and juvenile gets the point across just as well, if not better, as Colbert demonstrated when lampooning Donald Trump and his administration. Colbert has used drawings to explain everything from the Access Hollywood tape scandal to Republican Devin Nunes' conflict of interest. While the audience in the Ed Sullivan Theatre gets to see the whole work, at some point CBS will often blur out part of the image, prompting Colbert to playfully speculate as to just when that will happen.

#7: Tuck Buckford

“The Late Show with Stephen Colbert” (2015-)

Colbert has made a career out of parodying conservative pundits, but it turns out the host is willing to take it to the next level, imitating over-the-top conspiracy theorists like InfoWars host Alex Jones - which he does on the Late Show as Tuck Buckford. Colbert nails Jones’ mannerisms, his style of speaking, or rather shouting, and his far-out theories which, let’s be honest, don’t need to be exaggerated that much to play as comedy. The parody certainly made an impression, as the real Alex Jones brought up Colbert in his custody battle with his wife. Naturally, this shoutout only served as more fodder for the comedian.

#6: Colbert Election Coverage

“The Late Show with Stephen Colbert” (2015-)

Colbert’s 2016 Presidential Election coverage started as over-the-top humor, but ended on a very serious note. During the primaries, it was presented as the “Hungry for Power Games”, with Colbert in full Caesar Flickerman-inspired garb, giving a send-off to candidates who left the race as though they were fallen tributes. He also brought this character to both conventions, notably storming the stage at the RNC. Then, on election night, he hosted a live special called “Stephen Colbert's Live Election Night: Democracy's Series Finale - Who's Going to Clean Up This ****?” that very quickly turned from a comedy show into one of shock and reflection as the results poured in. Nonetheless… it was quality programming from beginning to end.

#5: Colbert vs. O’Reilly

Various

It’s clear that one of the inspirations for Colbert’s over-the-top conservative character on The Colbert Report was the bombastic now-former FOX News host Bill O’Reilly. In character, Colbert called him Papa Bear and when the two met in person on each other’s respective shows, Colbert’s mocking adoration was palpable. He promoted O’Reilly’s book on his show with a 30 percent off sticker and allegedly stole the microwave from the break room when he was a guest of the FOX host. When O’Reilly was fired, Colbert responded both in his old character and as himself, finally getting to say what he really thought of Papa Bear.

#4: Presenting at the Emmys

“58th Primetime Emmy Awards” (2006)

Colbert’s over-the-top character was at its best when paired with former Daily Show host Jon Stewart playing the straight man. This dynamic reached its peak when the pair co-presented at the 2006 Emmy Awards, in what was arguably one of the most memorable Emmy bits in the show’s history. As Stewart read a prepared script on reality shows from the prompter, Colbert, fully in character, laced into the assembled crowd of Hollywood celebrities, insulting them and saying that they pray to a golden idol, the Emmy statue. After the crescendo, Colbert jokingly admitted that it all had to do with his losing an award that evening to Barry Manilow. Classic Colbert.

#3: Putin’s Holster

“The Late Show with Stephen Colbert” (2015-)

Stephen Colbert is no stranger to controversy or mocking the administration. The two combined when the host decided to go after President Trump for his treatment of CBS journalist John Dickerson. The epic Late Show monologue rant that ensued culminated in a crude joke about Trump and Putin, which some initially characterized as homophobic. Colbert later apologized for his choice of words, but not for slamming Trump. With an army of Trump supporters criticising Colbert and eventually the President himself making a comment, Colbert was clearly satisfied with the controversy this bit caused.

#2: Burning Bush at the White House Correspondents’ Dinner

“WHCA Dinner” (2006)

In 2006, the White House Correspondents’ Association gave Colbert a chance to perform his faux-right wing George W. Bush-praising character for the man himself when they invited him to host their annual dinner. The Colbert Report host did not disappoint and most certainly did not hold back. He went after everything from Vice President Dick Cheney accidentally shooting a man in the face, to the Bush administration’s failing poll numbers, and the President’s track record of standing on aircraft carriers and “rubble” alike. Colbert even took part in a skit with the legendary White House correspondent Helen Thomas. Bush’s face throughout said it all - the man was hitting his mark.

#1: Colbert Super PAC

“The Colbert Report” (2005-14)

Some satirists tell jokes to highlight the problem of money in politics, but Colbert took things to an almost surreal level by starting his own political Super PAC capable of accepting large, anonymous donations for REAL. This gave him over a year’s worth of recurring material for his show, and quite a bit of information on the political funding process for his audience. He raised nearly $774,000, much of it from not so anonymous donors whose names rolled across the screen as heroes. In the end, on behalf of Ham Rove, his lunchmeat strategist, he donated the money to the Hurricane Sandy Relief Fund and groups fighting for campaign finance reform, among others.

Did we forget another unforgettable Colbert moment? Let us know in the comments below.