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From satirical political commentary to celebrity encounters, this comedian has made us laugh for decades! Join us as we count down our picks for the most hilarious Stephen Colbert moments. Our countdown includes his epic rap battles, memorable character work, political stunts, and unforgettable celebrity interactions that showcase his quick wit and comedic genius!
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00:00Stay strong, Papa Bear.
00:03Oh God, is this really happening?
00:06Welcome to WatchMojo, and today we're counting down our picks for the funniest parts of Stephen
00:10Colbert's vast comedy career.
00:19Number 20, teaming up with Jon Stewart and Jon Oliver, Night of Too Many Stars.
00:25Howie, what are you doing?
00:30That was me, Jon.
00:40That was me.
00:44While hosting this charity event, Jon Stewart couldn't do it alone.
00:47He utilizes multiple actors, comedians, and performers to make his monologue shine.
00:52This segment parody shows like America's Got Talent and The Curse of the Red Buzzer.
00:57This is all I wanted to do was bring people together tonight.
01:00I just wanted people.
01:01What is that?
01:09Jon, you're doing a terrible job.
01:11You're very bad.
01:12This is very bad.
01:13Stephen Colbert interjects early on, critiquing his old boss's performance and jokes.
01:18This is already funny before Jon Oliver even shows up.
01:21There's more than a few self-referential lines at the trio's expense, culminating in a shouting
01:26match.
01:27Stewart finally steps in to stop his former employees from hurting each other.
01:30If you're a fan of any of these three, you'll love seeing them interact and joking around
01:34again.
01:34Colbert, you are doing more or less what I'd expect for from a man who serves up his nightly
01:39joke meatloaf to an audience full of unsuspecting tourists herded from Bubba Gump Times Square.
01:46That's where your audience is from.
01:48That is not fair.
01:49It is fair.
01:49We also lure some of our audience from the M&M store.
01:52Well, that's...
01:52Let me tell you.
01:54Number 19.
01:55L.O.T.R. Rap.
01:57The Late Show with Stephen Colbert.
01:59Most fans of Stephen Colbert know that he's a massive Tolkien fan.
02:02Lord of the Rings Number One Trilogy of all time suckers.
02:07It's the Number One Trilogy, the Number One Trilogy.
02:10Try to deny and you just sound silly.
02:13Unable to pass up a good opportunity, the comedian did a hip-hop tribute to the Lord of
02:17the Rings films for their anniversary.
02:19This includes more than a few cameos from cast members and even Anna Kendrick.
02:23Best drill ever, baby, don't you forget.
02:25That's right, Anna Kendrick.
02:27Pitch Perfect A-
02:27What the hell?
02:31Why do we have friends?
02:33Damn.
02:34If you're not laughing at this crazy song, you'll be entertained by the frequent surprises.
02:38Method Man and Killer Mike also make appearances, along with a few other actors.
02:42Billionaire fights crime?
02:44I don't understand her.
02:45The Dark Knight's capitalistic propaganda.
02:48Colbert pulls out all the stops here as he embraces his rap alter ego.
02:52Along with some silly lyrics and references, the host makes a case for why these movies
02:56could be the best trilogy ever.
02:58Lord of the Rings is the Number One Trilogy.
03:01Movie's so sick, I gotta take an Advilie.
03:03When I'm sipping daffodillies, sipping chamomillies.
03:06Lord of the Rings is the Number One Trilogy.
03:09Number 18.
03:10Bruce Willis vs. Stephen Colbert.
03:12The Late Show with Stephen Colbert.
03:13A lot of action guys like Tom Cruise says, like, you know, they do all their own stunts.
03:19Do you, did you, did you ever, like, back in the day, did you do your own stunts?
03:22Of course.
03:24Really?
03:25I'd have to.
03:26Known for his action movie roles, Bruce Willis is a much tougher guy than Stephen Colbert.
03:30This all changes when the Late Show host asks about the actor doing his own stunts.
03:35The diehard star takes offense to Colbert's claims, with the two deciding to duke it out.
03:39You look tired, Bruce.
03:51Let me get you a chair.
03:55This leads to a choreographed fight full of thrills, spills, and over-the-top mayhem.
04:00Two other performers take over, making each maneuver look even more impressive.
04:09There's even some clever surprises here, like a drum set and a guitar.
04:23After a high fall, Willis finally admits that he's been lying after all.
04:27The last moment makes it all worthwhile, as a table dive seals the deal.
04:31I would do my own stunts.
04:33You son of a bitch!
04:37That would hurt!
04:39Bruce Willis, everyone!
04:41Number 17, Nicki Minaj's Colbert Rap.
04:44The Late Show with Stephen Colbert.
04:46Barbie Dreams, okay, is getting a lot of attention.
04:49Yeah.
04:49Okay, which is, as songs should, get a lot of attention.
04:52Yeah.
04:52This one's getting a lot of attention for some of the famous men you call out in this.
04:58With this rap star on the show, Stephen Colbert couldn't help but dive into her catalog.
05:03One question involves the celebrity men that Nicki Minaj mentions in her music.
05:07The host lets curiosity get the best of him.
05:09And I'm just curious that, um, if I were to make the list, what, how might, how might you inform me?
05:15Oh my god.
05:16Asking to be included on a list of famous guys.
05:19Minaj is quick to offer up a freestyle that embarrasses Colbert.
05:22The audience and even the band celebrate the moment, with the presenter hiding behind his note cards.
05:27I might f*** Stephen after the show.
05:29He's gonna come back to work with a magical glow, but.
05:42Kudos to the guest for being so fast and leaving the door open for this surprise.
05:46While the comedian is the farthest thing from a hip-hop icon, this is the closest he might come to the title.
05:51At the very least, the improvised verse and reaction is laugh-out-loud funny.
05:56It's all downhill from here.
06:00Number 16.
06:02Not Yet.
06:03The 37th Annual Kennedy Center Honors.
06:05Thank you so much.
06:06Back in 2014, Stephen Colbert prepared to leave his show at Comedy Central.
06:18He then became the heir to The Late Show on CBS.
06:20This prompted one of the funnier moments at the Kennedy Center Honors.
06:24With David Letterman presenting, Colbert decided to follow his predecessor on stage and stand next to him.
06:29It looked like Letterman might be replaced yet again by the younger comedian.
06:32With the audience in stitches, The Elder Presenter only needed to say one thing to make people happy.
06:41Not yet?
06:47The Colbert Report host ended up getting laughs without needing any dialogue at all.
06:52Number 15.
06:53Islam vs. Christianity.
06:55The Daily Show.
06:56If you were God, would you manifest your divine glory to a shepherd in a cave in Saudi Arabia in the 7th century?
07:04Or, as the son of a carpenter, in a manger in Judea in the year zero?
07:09Come on, use your mind.
07:11For the Eve and Stephen segment on The Daily Show, Stephen Colbert and Steve Carell face off in a religious battle.
07:17They have a playful discussion about both belief systems, while making themselves the butt of the joke.
07:21Colbert especially digs into Christianity, making funny asides about the line between faith and biblical literalism.
07:28First off, it's not my logic, Steve.
07:30It's God's logic.
07:31As written in the Bible, every word of which is true.
07:34And we know every word is true because the Bible says that the Bible is true.
07:39And if you remember from earlier in this sentence, every word of the Bible is true.
07:44Now, are you following me here?
07:46Or are you some kind of mindless zealot?
07:48Carell plays along while serving up some awesome rebuttals.
07:52Even if you're Muslim or Christian, you can still find plenty to chuckle about here.
07:56The clip also reminds you of how great these two were before they became superstars.
08:01Now, am I going to be doing that after I go to paradise to join my bevy of spotless virgins for all eternity?
08:07You know, because I just want to give them a heads up where I'm going for eternity.
08:11Guys, I'm sorry.
08:13I'm just starting to think that this religion thing, we're not going to settle it in three minutes.
08:15So if you just wrap it up and find some common ground, that would be great.
08:19Sorry.
08:21Both quick-witted and excellent performers, this duo proved that they're great friends and an amazing comedy team.
08:28Number 14, Prince Charles Report, The Daily Show.
08:32Meanwhile, across the pond in England, there's a much juicier scandal brewing, although I can't officially talk about it.
08:37In the 2000s, Prince Charles faced a rumor about an alleged relationship with a valet.
08:42The Daily Show tackles the subject with the exact amount of hilarity you'd expect.
08:47Correspondent Stephen Colbert wants to talk more about the allegations, but he's cautious about crossing any legal lines.
08:52Stephen, this has become a huge story overnight, but no one seems to know what these allegations are about.
08:59Have you been able to learn any of the specifics?
09:02Yes, I have, John.
09:08This leads him to use some funny double entendres and even bring out a prop.
09:12Colbert's choices with a banana are unforgettable and hilarious.
09:15Why don't you just come out and say there's an allegation that Prince had a gay experience?
09:21Your words, not mine, John.
09:24But I tell you this much.
09:26If it was substantiated...
09:31With even Stewart breaking at the sight of everything,
09:38the Daily Show presenter isn't afraid to go boldly into raunchy territory with reckless abandon.
09:43You know, mainly how gay it is.
09:54Number 13.
09:56Fighting Conan O'Brien and Jon Stewart.
09:58Late Night with Conan O'Brien.
10:00So back off of Mike Huckabee,
10:03or I will kick your translucent white ass.
10:10You got that, Irish?
10:11Back during a writer's strike in 2008,
10:14Late Night hosts needed a way to keep their shows going without a script.
10:17This led Stephen Colbert to throw down with Jon Stewart and Conan O'Brien in a comedic rivalry.
10:22With a goofy disagreement over Mike Huckabee,
10:25the trio of hosts ended up meeting on O'Brien's show to have a dramatic battle.
10:29If I see either one of these guys, I'm going to kick some serious Comedy Central ass.
10:33Right, everybody?
10:33I mean, that's just what's going to happen.
10:34The comedians then went into the hallway to start an all-out brawl.
10:52This included some fun nods to pro wrestling,
10:55with some entertaining stunts for added measure.
10:57It's especially funny to watch these men pretend to fall down stairs.
11:00Number 12, Friday Cover, Late Night with Jimmy Fallon.
11:22Almost anyone that remembers the early 2010s knows this tune.
11:38Rebecca Black's song inspired all kinds of tributes, critiques, and parodies.
11:43Stephen Colbert did his own version of Friday with some help from the Late Night with Jimmy Fallon staff.
11:47Fallon introduced the Colbert Report host,
11:50with the latter getting some backup from The Roots and American Idol winner Taylor Hicks.
12:02The cover goes from a moody introduction to a triumphant chorus.
12:06Even if you find the original annoying,
12:08this one reminds you that it's okay to enjoy a guilty pleasure.
12:11It's all delivered with the kind of comedic energy that'll have you laughing or singing along.
12:17There's even some dancers to bring it all home.
12:27Number 11, The Word Truthiness, The Colbert Report.
12:30Because you're looking at a straight shooter, America.
12:33I tell it like it is. I calls them like I sees them.
12:36I will speak to you in plain, simple English.
12:40At his peak, Stephen Colbert's character on The Colbert Report stood for his own kind of truth.
12:45This particular segment highlights this core attitude.
12:48The host leans towards his own gut instincts,
12:51telling viewers to not lean on any reference materials.
12:54It's a hilarious way to promote less reading and more ignorance.
12:57Who's Britannica to tell me the Panama Canal was finished in 1914?
13:02If I want to say it happened in 1941, that's my right.
13:06I don't trust books.
13:08They're all fact, no heart.
13:10Favoring feeling over brain power,
13:13the comedian mentions one controversial Supreme Court nomination from George W. Bush.
13:17The on-screen bumpers only give the audience more reason to think and laugh.
13:21But the president didn't say he thought about his selection.
13:26He said this.
13:27I know her heart.
13:30Notice how he said nothing about her brain.
13:33He didn't have to.
13:35He feels the truth about Harriet Myers.
13:38With the word being one of his most consistent bits,
13:41the presenter once again nailed the bravado of an opinionated pundit.
13:45With my help, you will.
13:46Well, the truthiness is anyone can read the news to you.
13:53I promise to feel the news at you.
13:57Number 10.
13:59Getting Daft Punk'd.
14:00The Colbert Report.
14:05While he likely didn't feel lucky at first,
14:08Colbert managed to turn a decision by Comedy Central's corporate parent Viacom
14:11to cancel an appearance by Daft Punk on The Colbert Report into comedy gold.
14:15After explaining how he'd only just found out the day before
14:18that another Viacom subsidiary, MTV,
14:21had exclusive performance rights to the French duo,
14:24he started dancing to Daft Punk's hit, Get Lucky.
14:27Various celebrities joined him in an original music video,
14:30most notably Breaking Bad star Bryan Cranston on roller skates
14:33in what looked like a disco.
14:39When life gives you lemons, you make a funny video.
14:42Number 9.
14:43Only in Monroe.
14:44Only in Monroe.
14:45Spoiler alert.
14:46Hope you didn't get too attached to that free parking on Cass Street.
14:49Stephen Colbert can host anything well.
14:52He proved it when, during the break between The Colbert Report and The Late Show,
14:55he took over hosting duties for one episode of a local Monroe,
14:58Michigan public access show.
15:00Only in Monroe.
15:01If you're wondering what muskrat tastes like,
15:03imagine eating a rat, but with more musk.
15:06He interviewed the show's regular hosts
15:08and brought up a very local and impressively out-of-date Yelp review
15:12before introducing his special guest, Michigan native Eminem,
15:16whom Colbert referred to by his given name, Marshall Mathers.
15:19Marshall, thanks so much for being here today.
15:21After pretending not to know his guest was famous,
15:23the pair co-presented the ultimate local show segment,
15:26a real Monroe, Michigan community calendar.
15:28Stop by if you're a numismatist,
15:30or if Tuesday is laundry day and you just need to break a single.
15:33Number 8.
15:34Crude Political Drawings.
15:36The Late Show with Stephen Colbert.
15:38I'm writing osiates really small because I don't want to waste chalk here.
15:42Colbert's political comedy can be witty highbrow satire,
15:45but sometimes downright crude and juvenile gets the point across just as well,
15:49if not better,
15:50as Colbert demonstrated when lampooning Donald Trump and his administration.
15:53Probably because Obama is a Muslim, and that's a bad thing.
15:58Colbert has used drawings to explain everything,
16:01from the Access Hollywood tape scandal,
16:03to Republican Devin Newton's conflict of interest.
16:05While the audience in the Ed Sullivan Theater gets to see the whole work,
16:09at some point, CBS will often blur out part of the image,
16:12prompting Colbert to playfully speculate as to just when that will happen.
16:16Right there! Right there!
16:18Number 7.
16:20Tuck Buckford.
16:21The Late Show with Stephen Colbert.
16:22Listen, people, the liberals want to tattoo Obama logos
16:27onto the skin of Christian babies, okay?
16:31Colbert has made a career out of parodying conservative pundits,
16:34but it turns out the host is willing to take it to the next level,
16:37imitating over-the-top conspiracy theorists,
16:40like InfoWars host Alex Jones,
16:42which he does on The Late Show as Tuck Buckford.
16:44I'm a father! I have male vitality!
16:47My children flew out my penis like a flame of love!
16:51Colbert nails Jones' mannerisms,
16:54his style of speaking, or rather, shouting,
16:56and his far-out theories, which, let's be honest,
16:59don't need to be exaggerated that much to play as comedy.
17:02The parody certainly made an impression,
17:04as the real Alex Jones brought up Colbert
17:06in his custody battle with his wife.
17:08Naturally, this shout-out only served as more fodder for the comedian.
17:11I'm a marijuana addict who should not be trusted with my own children.
17:16Number 6. Colbert Election Coverage
17:18The Late Show with Stephen Colbert
17:19No, obviously, I'm very grateful that you're here.
17:22I'm gonna finish this reel.
17:23You can finish mine, too.
17:25Colbert's 2016 presidential election coverage
17:27started as over-the-top humor,
17:29but ended on a very serious note.
17:31During the primaries,
17:32it was presented as the Hungry for Power games,
17:35with Colbert in full Caesar Flickman-inspired garb,
17:38giving a send-off to candidates who left the race
17:41as though they were fallen tributes.
17:45He also brought this character to both conventions,
17:48notably storming the stage at the RNC.
17:51Then, on election night,
17:52he hosted a live special called
17:54Stephen Colbert's Live Election Night Democracy Series Finale
17:57Who's Gonna Clean Up This Shit?
17:59that very quickly turned from a comedy show
18:01into one of shock and reflection
18:02as the results poured in.
18:04Let me ask you a technical question
18:06that you guys, being political analysts,
18:08would know, you'd understand.
18:10Uh, what the f*** is happening?
18:12Nonetheless, it was quality programming
18:14from beginning to end.
18:15Welcome, citizens, to the 2016 100 for Power Games!
18:20Number 5.
18:22Colbert vs. O'Reilly
18:23Various
18:24So it doesn't happen again, Colbert!
18:26Okay, takeaway, takeaway.
18:28Was it the right thing to do?
18:29It's clear that one of the inspirations
18:31for Colbert's over-the-top conservative character
18:33on The Colbert Report
18:34was the bombastic now-former Fox News host,
18:37Bill O'Reilly.
18:37It is tough being me.
18:38Is it tough being you?
18:40In character, Colbert called him Papa Bear,
18:43and when the two met in person
18:44on each other's respective shows,
18:46Colbert's mocking adoration was palpable.
18:48He promoted O'Reilly's book on his show
18:50with a 30% off sticker,
18:51and allegedly stole the microwave
18:53from the break room
18:54when he was a guest of the Fox host.
18:56When O'Reilly was fired,
18:57Colbert responded both in his old character
18:59and as himself,
19:01finally getting to say
19:01what he really thought of Papa Bear.
19:03Stay strong, Papa Bear!
19:05Number 4.
19:06Presenting at the Emmys
19:0758th Primetime Emmy Awards
19:10Good evening, godless sodomites.
19:12Colbert's over-the-top character
19:14was at its best
19:15when paired with former Daily Show host
19:17Jon Stewart playing the straight man.
19:18This dynamic reached its peak
19:20when the pair co-presented
19:21at the 2006 Emmy Awards
19:23in what was arguably
19:24one of the most memorable Emmys bits
19:26in the show's history.
19:27I'm reading the prompter in here.
19:29You can read that pablum.
19:32As Stewart read a prepared script
19:33on reality shows from the prompter,
19:35Colbert, fully in character,
19:37laced into the assembled crowd
19:38of Hollywood celebrities,
19:40insulting them
19:40and saying that they pray
19:41to a golden idol,
19:43the Emmy statue.
19:44Kneel before your god, Babylon!
19:47After the crescendo,
19:49Colbert jokingly admitted
19:50that it all had to do
19:51with his losing an award that evening
19:52to Barry Manilow.
19:54Classic Colbert.
19:55I lost to the Copacabana!
19:57Number 3.
19:59Putin's Holster.
20:00The Late Show with Stephen Colbert.
20:02You're not the POTUS,
20:03you're the BLOTUS.
20:05Stephen Colbert is no stranger
20:06to controversy
20:07or mocking the administration.
20:08The two combined
20:09when the host decided
20:10to go after President Trump
20:11for his treatment
20:12of CBS journalist
20:13John Dickerson.
20:14John Dickerson
20:15is a fair-minded journalist
20:17and one of the most competent people
20:18who will ever walk into your office
20:20and you treat him like that?
20:22The epic Late Show monologue rant
20:23that ensued
20:24culminated in a crude joke
20:26about Trump and Putin,
20:28which some initially characterized
20:29as homophobic.
20:30In fact,
20:30the only thing your mouth
20:31is good for
20:32is being Vladimir Putin's
20:33*** holster.
20:34Colbert later apologized
20:35for his choice of words,
20:37but not for slamming Trump.
20:38With an army of Trump supporters
20:40criticizing Colbert
20:41and eventually the president himself
20:42making a comment,
20:44Colbert was clearly satisfied
20:45with the controversy
20:46this bit caused.
20:47I don't regret that.
20:48Number 2.
20:49Burning Bush
20:50at the White House
20:50Correspondents Dinner,
20:52WHCA Dinner.
20:53The president in this case
20:54is Rocky Balboa
20:55and Apollo Creed
20:57is everything else in the world.
21:00In 2006,
21:01the White House
21:02Correspondents Association
21:03gave Colbert a chance
21:04to perform his faux right-wing
21:06George W. Bush
21:07praising character
21:07for the man himself
21:09when they invited him
21:10to host their annual dinner.
21:11The Colbert Report host
21:12did not disappoint
21:13and most certainly
21:14did not hold back.
21:15This administration
21:17is not sinking.
21:18This administration
21:19is soaring.
21:21He went after everything
21:22from Vice President
21:22Dick Cheney
21:23accidentally shooting
21:24a man in the face
21:25to the Bush administration's
21:26failing poll numbers
21:27and the president's
21:28track record
21:29of standing on
21:29aircraft carriers
21:30and rubble alike.
21:32Colbert even took part
21:33in a skit
21:33with the legendary
21:34White House Correspondent
21:35Helen Thomas.
21:36Bush's face throughout
21:37said it all.
21:38The man was hitting his mark.
21:42Before we continue,
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21:59Number 1.
22:00Colbert Superpack
22:01The Colbert Report
22:02Some satirists tell jokes
22:04to highlight the problem
22:05of money in politics,
22:07but Colbert took things
22:08to an almost surreal level
22:09by starting his own
22:10political superpack
22:11capable of accepting
22:12large, anonymous donations
22:14for real.
22:15This gave him
22:21over a year's worth
22:21of recurring material
22:22for his show
22:23and quite a bit
22:24of information
22:25on the political funding
22:26process for his audience.
22:27He raised nearly
22:28$774,000,
22:30much of it
22:31from not-so-anonymous donors
22:32whose names rolled
22:33across the screen
22:34as heroes.
22:35In the end,
22:36on behalf of Ham Rove,
22:37his lunchmeet strategist,
22:39he donated the money
22:39to the Hurricane Sandy
22:40Relief Fund
22:41and groups fighting
22:42for campaign finance reform,
22:44among others.
22:49Did we forget
22:50another unforgettable
22:51Colbert moment?
22:52Let us know
22:53in the comments below.
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