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Get ready to laugh until it hurts! Join us as we count down the most hilarious moments from the legendary career of Conan O'Brien! From unforgettable talk show sketches to legendary guest appearances, we're celebrating the comedic genius that kept us glued to our screens for decades. What's your favorite Conan moment? Let us know in the comments below!
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00:00Well, folks, there is one clip from Walker, Texas Ranger that we've been holding back on.
00:05In fact, this is true. We've been afraid to show it.
00:09Welcome to WatchMojo, and today we're looking at Conan O'Brien's funniest moments ever committed to the screen.
00:20Sit perfectly still. Only I may dance.
00:26Number 20. Party Photos. Late Night with Conan O'Brien.
00:30Conan had some of the most memorable recurring bits in Late Night, from in the year 2000 to casting for
00:36made-for-TV movies.
00:37They just finished casting this show, and apparently they don't want anyone to know who's playing whom, but I found
00:44out.
00:45I actually wandered by the casting offices. I got the list of who's going to play who, and I'm going
00:49to tell you because it's a big scoop, and what do I care?
00:52We especially loved it when Conan shared photos from his various parties.
00:55You can tell these were not real based on the shoddy backgrounds, amateurish photoshopping, and exaggerated expressions, but that only
01:03made these visuals funnier.
01:05Conan mugged in front of the camera with drummer Max Weinberg and announcer Joel Goddard.
01:09The two played fictionalized versions of themselves, with Max as a sleazebag and Joel as a straight-up weirdo.
01:15Joel Goddard gave him something for after the concert.
01:19Yeah, he...
01:20Max reminded Joel of his strict no-condom policy.
01:28And, uh...
01:30Always good to have that sign hanging up on the wall.
01:32Conan's descriptions of the photos were just as hysterical, often calling out how ridiculous he and his co-workers appeared.
01:39Of course, what we want to know is who was taking the photos.
01:43Is that where Andy went?
01:45Number 19.
01:46Dana Carvey's Micro Impressions.
01:48Conan.
01:49For this appearance, the Saturday Night Live legend joins Conan O'Brien for a versatile segment.
01:54Sean Connery is being asked whether he would like to vacation in Spain, okay?
01:59And he just says, yeah, shh.
02:02He practically turns his time into a stand-up set with enough jokes to fill a full special.
02:07Carvey reminds everyone of his gift for impressions, never missing a beat with a wide variety of celebrity voices.
02:14These include funny interpretations of everyone from Sean Connery to Bernie Sanders.
02:18Bernie Sanders, this is new.
02:20Bernie Sanders on the Pirates of the Caribbean ride.
02:22This is rigged!
02:23The whole system is rigged!
02:25The pirates aren't real!
02:27The beauty of these routines is that the comedian only uses a few words at a time.
02:32Knowing when to step back and let his guest thrive, O'Brien lets the comic perform and
02:37provides some hearty laughs in the process.
02:39I do Michael Caine in kindergarten.
02:41Oh, yeah?
02:43It's already funny!
02:45Why do we have to draw between two lines?
02:49Number 18.
02:50Conan Steps Up to Vintage Baseball.
02:52Late Night with Conan O'Brien.
02:53Conan fares well in old-timey environments.
02:57This time, he goes back to 1864 to check out an authentic baseball scene.
03:02Well, authentic-ish.
03:03We learn that farmers are super into the sport, and Conan learns some 1864 baseball lingo.
03:09First of all, a pitcher is called a hurler.
03:11Fans are cranks, rooters, birds, and bugs.
03:16That's correct.
03:16We also meet some of the team's biggest fans, like this woman who, despite Conan's best
03:22efforts, never breaks character.
03:24She even manages to break him.
03:26Oh, there you go.
03:26He's a tailor.
03:27He makes clothes for the farmer.
03:29And what about you?
03:30He's a farmer.
03:31Farmer?
03:31And your father?
03:32My father's passed.
03:36Honestly, her commitment to the role creates the most hilarious back and forth.
03:41Of course, things reach a new level of unhingedness when Conan fully embraces the times and joins
03:47the game.
03:48We just hope the real 1864 team had someone like Conan to pump them up before a match.
03:53Then take both hands and give you a massage just to loosen you up.
03:57Now, let's get back out there and show that other team why our life expectancy is only 39
04:04years.
04:04Number 17, Quackers, Late Night with Conan O'Brien.
04:08Conan is at his best when a bit goes completely wrong and he just rolls with it.
04:13Such was the case with a duck that Conan named Quackers on the spot.
04:17What started as a standard sketch sprang to life when Quackers entered.
04:21There wasn't anything particularly unique about this duck, but audiences instinctively respond
04:26to cute animals.
04:27I should have had the duck at the end of the sketch, not the top.
04:30I can't stop looking at him.
04:32All right.
04:33In another episode, Conan brought Quackers back simply to fill airtime.
04:37The routine purposely didn't seem to be going anywhere until Quackers defecated in front
04:42of the audience and tasted it.
04:44Conan reacted precisely how you would expect Conan to respond.
04:48What the hell was that?
04:50I thought I was doing a nice thing.
04:51Let's just bring out.
04:52I thought this would be the one clean portion of our show.
04:56Suddenly, Conan went from having little to work with to a lot.
05:00He ate it up, just as Quackers ate feces.
05:08Some of the funniest and most chaotic moments take place backstage at Conan HQ.
05:12Watching him hang out with the interns is a riot.
05:15This guy was blown away that you know Conan.
05:18No, no, no.
05:18And you were like, he's very tall and he has a long stride.
05:24Meanwhile, if we had our annual reviews with him, we'd probably look forward to them.
05:30And tell us you wouldn't get all Conan on your colleagues if you found out they were
05:33bogarting free food.
05:34I was watching, we had closed circuit cameras watching.
05:38You came in the room and you went right for the cake.
05:42Other people kind of walked around shy.
05:44You went right for the cake and cut into it.
05:46Still, perhaps nothing is funnier than his commitment to helping his assistant Sona track
05:51down her missing mug.
05:52Did you take it?
05:53I did not.
05:53You're a liar.
05:54I'm not a liar.
05:55You took the mug.
05:55Did not take the mug.
05:56Took the mug.
05:57Why would I take the mug?
05:57Why did you take the mug?
05:58Did not do it.
05:59Okay, tell me you did it and I won't fire you.
06:01Didn't do it.
06:01Okay.
06:02All right, so you're going to stick to your story.
06:03While conducting his investigation, he ends up learning a lot about the people who
06:07work for him.
06:08Eventually, he tracks down the missing item.
06:10But there's an unexpected plot twist.
06:13This is incredible.
06:13So you're clearly innocent.
06:14This isn't your fault.
06:15An intern brought it to you.
06:17Correct.
06:18And now it's my job to see that an unpaid intern is fired.
06:24Is Sona grateful for the returned mug?
06:27Number 15.
06:28Adam Sandler Interrupts Chris Farley.
06:30Late Night with Conan O'Brien.
06:32Among the brightest comedy stars of the 1990s, Chris Farley had a way of lighting up any
06:37room.
06:38This Late Night with Conan O'Brien appearance helps him do that while also capturing the
06:42performer at a career high point.
06:44Do you think Newt Gingrich is going to make it?
06:45Do you think he's going to do a good job as speaker?
06:48Do you think he's going to go all the way?
06:52Conan, I'm not much of a reader.
06:54He also fondly mentions an impression of Newt Gingrich and reveals his lack of knowledge
06:59about real politics.
07:00After the conversation steers towards his love life, Farley tries to woo an audience member.
07:05You sure are pretty.
07:09My name's Chris Farley from Muitani Boy.
07:13His comedic timing makes this awkward moment really memorable, but there are even more
07:18surprises in store.
07:19Adam Sandler bursts in like a jealous lover, prompting some amazing reactions from his
07:24counterpart.
07:35It's ultimately a quick skit that is absurd in the best possible way.
07:44When you work with Conan O'Brien, even the most unlikely individuals can become stars.
07:49Pierre Bernard is a graphic designer by day, but by night, Conan gave him a recliner of
07:55rage.
07:56This is the most powerful nation on earth.
07:58Can't we figure out a way to refrigerate Malamars properly?
08:03With Bernard regularly appearing in sketches, Conan thought it would be funny if the crew
08:07went to his house and looked at his collectibles.
08:09For all the absurd things Bernard had done for the show, this is where he drew the line.
08:14To Conan, this could only mean one thing.
08:17Pierre is a serial killer.
08:19Interviewing the Stargate fan, Conan attempted to coerce a confession out of Bernard.
08:24Putting words in his mouth and incorporating creepy music, their sit-down is as chilling
08:32as it is silly.
08:34Bernard remains at large.
08:39With Conan's original late-night show taping at 30 Rockefeller Plaza, it seemed inevitable
08:44that he would drop by Tina Fey's sitcom.
08:46One episode revolves around Faye's Liz Lemon trying to get a whacked-out Tracy Jordan ready
08:51for an interview with Conan, who already had one disastrous experience with the comedian.
09:00As humorous as Conan's scenes are with Tracy, the real gold is his dynamic with Liz.
09:05In the show's universe, Conan and Liz used to be an item.
09:08They learn little about their romance, but you can tell there were hard feelings.
09:12In another episode, a flashback reveals that they never consummated their year-long courtship.
09:26Conan is married now, although he's apparently still a virgin in the show's canon.
09:31Number 12, Conan Kills Some Time, Late Night with Conan O'Brien.
09:35We have no writers and we have an hour show, a one-hour show to do every night.
09:40Well, ladies and gentlemen, we're going to start by talking about my beard.
09:45Moments like this make us wish Conan O'Brien was still on Late Night.
09:48During the 2007-2008 writer strike, the host, an adept writer himself, sought to highlight
09:54how important writers are by deliberately letting the show go off the rails.
09:58Nothing would end this strike faster.
10:02The producers, the studio heads would see that, give the writers whatever they want!
10:08Make that ass stop dancing!
10:10Both admirable and hysterical, O'Brien decided to showcase something he would do during rehearsals.
10:16He took off his wedding ring and spun it on his desk.
10:19Conan gave us a rundown of the stakes at play and the obstacles he had to overcome,
10:23like a slanted surface to try and break his record of 41 seconds.
10:26I know ring spinning, 41.
10:29Pretty good!
10:31While maybe he didn't win the Great Wedding Ring Spinning Contest of 2008,
10:36he somehow warmed our hearts and tickled our funny bones.
10:3936 seconds!
10:45Number 11.
10:46Becoming a Driver Instructor Alongside Ice Cube and Kevin Hart.
10:50Conan.
10:50How many people can say their bosses taught them how to drive?
10:53Fewer can probably say they were instructed by Conan, Ice Cube, and Kevin Hart.
10:58It's a recipe for chaos, as the latter two bring profanity-fueled road advice
11:03that would be better left at the curb.
11:15For instance, we don't imagine many driving lessons include stopping off for,
11:20ahem, recreational supplies, although it makes Hart's chat with the cop that much funnier.
11:25What I learned is that Jesus once walked on water.
11:30I don't know where I'm going with this, guys.
11:32By the end, wrapping up at Popeye's seems like the only logical conclusion.
11:37This isn't the only time the trio gets in a car together.
11:40And honestly, the fact that it didn't blow up like other famous car segments is a comedic injustice.
11:45Wait a minute, where's the brown paper bag?
11:47Man, Conan, you don't just get rid of the brown s**t.
11:49Where's the brown paper bag?
11:50I can't drink this.
11:53You didn't say anything about the brown paper bag.
11:55Number 10.
11:56Addressing Harvard Class.
11:58Thomas Francis O'Brien, Conan's father, was a professor at Harvard Medical School.
12:03Conan also attended Harvard, naturally choosing a different career path than his dad.
12:08In 2000, Conan returned to his alma mater to address the graduating class.
12:1215 years ago, I sat where you sit now.
12:16And I thought exactly what you are now thinking.
12:20What's going to happen to me?
12:22Will I find my place in the world?
12:26Am I really graduating a virgin?
12:29Conan seized this moment to read the commencement speech he never got to share.
12:33Reflecting on his college days, Conan delivered his trademark self-deprecating humor while also
12:38taking playful jabs at the university itself.
12:41Life after Harvard isn't as glamorous as it seems.
12:44Conan detailed his post-grad struggles, but the speech builds to an inspiring climax as
12:49he quotes a review that praised him as a comedic genius.
12:52Somehow Conan O'Brien has transformed himself into the brightest star in the late-night firmament.
12:57His comedy is the gold standard, and Conan himself is not only the quickest and most
13:01inventive wit of his generation, but quite possibly the greatest host ever.
13:07Ladies and gentlemen, class of 2000, I wrote that this morning.
13:14Although it turned out Conan wrote that himself, he got his point across.
13:18Failure is part of success.
13:20Number 9.
13:21Reacting to Pale Force, Late Night with Conan O'Brien
13:24In the 2000s, comedian Jim Gaffigan collaborated with cartoonist Paul Noth to make an animated
13:30web series, Pale Force.
13:31Gaffigan voiced himself and a high-pitched Conan, who team up to fight crime with their
13:36paleness and laser-shooting nipples.
13:38But if it wasn't you saying those things, who was it?
13:41I don't know, little buddy.
13:43I don't know.
13:44Warning.
13:45Warning.
13:46Warning.
13:47Conan.
13:48Save yourself.
13:50Okay.
13:51The cartoon was basically an excuse for Jim to troll Conan, depicting him as cowardly,
13:56weak, not very bright, and a pants-weather.
13:58While Pale Force was funny, the real Conan's reactions were priceless.
14:03Against his better judgment, Conan repeatedly invited Jim back to share new episodes.
14:08While Conan was always a good sport, that doesn't mean he didn't call Jim out over his portrayal.
14:13Even on Conan's own show, it felt like Gaffigan had more control whenever he showed up armed
14:18with another Pale Force.
14:19It was Charlie Brown, Lucy, and the football, over and over and over again.
14:22It was really fun.
14:23Nice to take that trip down Humiliation Lane.
14:26Number 8.
14:26Crashing the Emmys, the 58th Primetime Emmy Awards
14:30Conan has become the Academy's go-to Oscar host in recent years.
14:34The Emmys previously proved that Conan was up to the task.
14:37After the Osbournes helped him get ready in 2002,
14:40Conan topped himself at the 2006 Primetime Emmys.
14:54The show's opening was both a celebration and a satire of the past year in television,
14:59with Conan crash-landing on a familiar island.
15:01Conan isn't the only one who can't believe Lost wasn't nominated,
15:05but he has other mysteries to solve, like what's in the hatch.
15:08Turns out, it's an entrance to Dunder Mifflin.
15:10Making his way to the ceremony,
15:12Conan also encounters Jack Bauer, Dr. House, and Tom Cruise in Stan's Closet.
15:17Conan can't seem to catch a break, although Chris Hansen catches someone.
15:31For a period in 2007, Conan took his show to San Francisco.
15:36He found the time for some sightseeing and people-watching.
15:39You're excited about the show?
15:40Yeah, yeah, yeah, yeah, yeah.
15:42Are you gonna watch the show?
15:43Yeah, I've watched the show, yeah.
15:44Is he lying to me or is he telling the truth, you think?
15:46He's telling the truth, right?
15:48Oh, I think so.
15:49But there's a particular landmark that Conan is most interested in visiting.
15:53The Full House House.
15:54Conan not only tracks down the historic house used for the sitcom's exterior shots,
15:58but someone is waiting inside.
16:00It's Danny Tanner himself, Bob Saget,
16:03who's still living there more than 10 years after the series ended.
16:05He tags along with Conan as they recreate the Full House intro,
16:09complete with theme song and title cards.
16:11Saget also shows that he is not as family-friendly as his character.
16:15So what else is there to see in San Francisco, Bob?
16:17There's so much here, Conan.
16:18There's the Exploratorium, there's the Japanese Tea Garden,
16:21there's the Palace of Fine Arts, there's the DeYoung Museum,
16:25there's the Opera House, there's the Symphony,
16:27and then there's this place, the Mitchell Brothers Lodge Sextator.
16:34Forget Fuller House, this is the revival that we deserved.
16:43When Norm Macdonald came on a talk show,
16:45there was no telling what he would say or do.
16:48This made for great television,
16:49such as this highlight from Late Night with Conan O'Brien.
16:52Can you put the picture up of Carrot Top again,
16:54just so we can all see him?
16:55Oh, there it is, again, yeah.
16:56There it is!
16:57All right, okay.
16:59Wait a minute, she left Melrose Place to do a movie with Carrot Top?
17:03The comedian uses every opportunity to butt into the interview
17:06with his trademark humor.
17:07He even finds time to bash Courtney Thorne Smith's career choices.
17:11What? I know what it's going to be called.
17:13Yeah, what's that?
17:15If it's got Carrot Top in it, you know what a good name for it'd be?
17:18What's that, Norm?
17:19Box office poison.
17:20The segment also includes him making fun of her movie
17:23with the comedian Carrot Top,
17:25with a moment that ranks among McDonald's finest one-liners.
17:28Chairman of the board.
17:30Oh, all right.
17:31Do something with that, you freak.
17:36I bet the board is spelled B-O-R-E-D.
17:40O'Brien can't stop the train before it goes off the tracks,
17:43and we thank him for it.
17:48Apparently, O'Brien was a hot commodity among Hot Ones fans,
17:52and he was determined to bring the heat.
17:54It's got to build.
17:55It's starting to build right now.
17:56Yeah, yeah.
17:57Oh, it's building.
17:58Yeah.
17:59And it's kind of not going to stop.
18:01No, it's not going to stop.
18:02But that's okay.
18:03Indeed, the show has seen its fair share of wild reactions,
18:07but O'Brien's take is arguably the Matasano's hot sauce of the entire series.
18:11At first, he questions if his Irish taste buds can handle it.
18:15I don't think there's a wing here that I can't eat like it's ice cream.
18:18I seriously, I don't think there's a wing on this table that I cannot devour like it's
18:24cool whipped cream.
18:26Yet he confidently powers through, essentially turning every moment into the Conan show.
18:31However, things truly go off the rails when the heat starts to get to him.
18:35I don't have a lot of regrets in my career.
18:38Pouring this onto the wing.
18:39Right.
18:40And then licking it off.
18:41And in retrospect, I bet you it's good footage.
18:45No, yeah.
18:46It's good TV.
18:47Um, I'm starting to feel some sensation.
18:50From then on, everything descends into anarchy.
18:53It definitely brings a whole new meaning to masking your pain with humor.
18:57It's a meme-worthy level of Unhinged, and we are very here for it.
19:02You didn't come up with one wing that had any effect on Conan.
19:06Because he's here to stay.
19:09Awoo!
19:11Awoo!
19:12Number 4.
19:13Conan Runs.
19:14The Tonight Show with Conan O'Brien.
19:16Conan's tenure as The Tonight Show host deserved a much longer run.
19:20How long?
19:21However long it takes to run from New York to Los Angeles.
19:24Conan has experience on that front, opening his first Tonight Show episode with this pre-taped bit.
19:29Build a set.
19:31Write jokes.
19:32Get dressed.
19:34Brush teeth.
19:35Check.
19:36Move to L.A.
19:38Ready to make his debut, Conan realizes he forgot to do one tiny thing.
19:43Move across the country.
19:45Unable to catch a cab to the airport, Conan runs from the Big Apple to Tinseltown, passing through a few
19:50other states.
19:51The accompaniment of Cheap Trick's Surrender gives the montage an epic sentiment,
19:55but the segment builds to a classic Conan punchline as he realizes his keys are back in New York.
20:08That's still not going to stop Conan, although NBC's incompetence might.
20:16In 2009, Conan succeeded Jay Leno as host of The Tonight Show.
20:22But in a surprising turn, NBC reinstated Leno the next year.
20:27It was a PR nightmare from start to finish.
20:29You know, I know you meant well, but I had The Tonight Show for 10 minutes, and you just ate
20:33into my time.
20:35We'll give you time.
20:36This is all the time I have.
20:38Knock it off!
20:39Still, Conan was determined to leave his mark, and it would cost NBC a lot.
20:45I knew it, and they have to pay for it.
20:47So, for the rest of the week, we're going to introduce new comedy bits that aren't so much funny as
20:54they are crazy expensive.
20:55With nothing to lose, he decided to go all out and blow the budget.
21:00Until this moment, we didn't even know we needed to see a Bugatti dressed as a mouse with the Rolling
21:05Stones blaring in the background.
21:07Is this appropriate music for a car that looks like a mouse?
21:10No!
21:11Does it add anything at all to this comedy bit?
21:14No, it doesn't!
21:16Is it crazy expensive to play on the air?
21:19The whole stunt reportedly cost $1.5 million.
21:22But can you really put a price on this level of wild entertainment?
21:27It is pure, unadulterated hilarity, and we are here for every penny spent.
21:32That's right, ladies and gentlemen.
21:34Total price tag for this comedy bit, $1.5 million!
21:42Number 2.
21:43Paul Rudd's prank.
21:45Various.
21:45This might be the longest-running prank in talk show history.
21:49At the very least, it's one of the funniest gags in the history of Conan O'Brien's television career.
21:54Didn't see it going that way.
21:56There's a lot of surprises in the last episode.
21:58Wow.
21:59It was pretty emotional.
22:00I mean, as you can see, Matthew Perry was in a wheelchair for the last episode.
22:05Paul Rudd's guest spots almost always include a moment for him to show off his latest film.
22:10Instead of promoting the movie, he plays a clip from the E.T. ripoff, Mac and Me.
22:14You've been showing that stupid clip on my show for, I think, 15 years.
22:21It's from a movie called Mac and Me.
22:24It's such a ridiculous scene that it always gets a laugh no matter how many times it plays.
22:29Rudd's dedication to the bit never ceases to impress after all these years,
22:33turning a funny premise into a legendary piece of O'Brien's legacy.
22:37So you can see why it bombed.
22:41I didn't think...
22:42Whoever dies first, you have to do that at the other one's funeral.
22:45Yeah, yeah, yeah.
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23:01Number 1. Walker Told Me. Late Night with Conan O'Brien.
23:05Before we watched out-of-context clips from old TV shows on YouTube,
23:09Conan O'Brien arguably started the trend with his giant lever.
23:12He can only play clips from one TV show, however.
23:15Walker, Texas Ranger, starring Chuck Norris.
23:17All I have to do is pull the Walker, Texas Ranger lever,
23:20and we're immediately treated to a Walker, Texas Ranger clip.
23:25While the random clips brought us no shortage of unintentionally hilarious moments,
23:30one stands out above all others.
23:32It features a young Haley Joel Osment just two years before The Sixth Sense.
23:36What starts as a charming exchange abruptly takes a dark turn as Osment's character says,
23:42Walker told me I had AIDS.
23:49And that's where the clip ends.
23:51Conan appears mortified that he ever pulled the lever,
23:54walking off into the distance as he rethinks his life.
23:56You might not be proud of yourself for laughing,
23:59but this clip gets us every time.
24:02What's your favorite Conan O'Brien moment?
24:04Let us know in the comments.
24:05We'll see you next time.
24:10Amen.
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