Top 10 Funniest Conan O'Brien Interview Moments
Nobody does an interview like Conan. Welcome to MsMojo, and today we’re counting down our picks for the most hilarious and memorable interview segments from Conan’s career.
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00:00 give me any question from history and I, I proved to you I'm a moron."
00:04 Welcome to Ms. Mojo, and today we're counting down our picks for the most hilarious and
00:10 memorable interview segments from Conan's career.
00:13 -I love you Conan! -I love you too sir.
00:15 Number 10. Simon Helberg does Robin Williams.
00:20 Known for his roles in shows like 'The Big Bang Theory,' Simon Helberg is also a skilled
00:25 impressionist. His work as Robin Williams really excites the Conan audience and its host.
00:31 "Doing all the off-the-wall stuff and then I sort of became fascinated with his,
00:35 his very serious side, you know, he's always talking about the gift of laughter, chief."
00:41 Not only does Helberg nail the chaotic version of Williams,
00:45 he's able to slow everything down for a more subdued impression.
00:48 The TV star's accurate portrayal of the goodwill hunting side of the comedian
00:53 feels just as believable as the crazier one.
00:56 "I want to go to Darfur with, you know, just give them the gift of laughter.
00:59 It's, you know, you know, you know, it can't help but get a little bit, oh, but,
01:04 but you know, to bring it down."
01:06 Altogether, this segment turns into a showcase of the guest's dynamic ability as a mimic and
01:12 physical performer. Once he stands up, the actor unleashes a variety of hilarious voices in a
01:18 whirlwind performance.
01:20 "Right now Gandhi is somewhere going, 'Oh my God, if only I had known, but if I--'
01:23 [Laughter]
01:24 'Who said that? Not me, okay. Say hello to Mr. Happy.'
01:29 [Laughter]
01:30 Number 9.
01:31 Jennifer Garner - Grammar Police
01:33 Jennifer Garner and Conan O'Brien are having a friendly conversation
01:38 until the subject of grammar comes up.
01:40 "But um, there was a day last year when I kind of...
01:44 Sneaked my way in."
01:47 The actress attempts to correct the host after the latter uses the past tense version of "sneak."
01:53 Trying to catch O'Brien in a mistake,
01:56 Garner calls him out in a moment that draws a strong response from the crowd.
02:00 "There's a time when you snuck into the room to see what the--"
02:02 "I, I, I sneaked into the room. Snuck isn't a word, Conan, and you went to Harvard and
02:05 you should know that."
02:06 A typical show might have kept going on without mentioning the incident again.
02:11 This particular program decides to have a callback later on,
02:14 with the presenter bringing out a book for reference.
02:17 "I keep a dictionary down here and I just found it. I just want to look at--
02:20 Oh, what the hell, look right here! Snuck, past and past part of sneak."
02:26 He confirms that "snuck" is a word, and gets the last laugh in a dramatic finale.
02:32 Number 8.
02:34 Martin Short mocks Conan
02:36 One of the most celebrated talk show guests of all time,
02:39 Martin Short has created a persona as an insult comic.
02:43 "I, I'm an order of Canada. It's, it's like Canadian knighthood. But I know enough about
02:48 me. I want to hear about you and how you got started and everything."
02:50 He channels the likes of Don Rickles in this appearance on the Conan show.
02:54 Rather than stopping him, the host lets Short run wild with jokes about the presenter's program,
03:00 career, and more.
03:02 "He's in Madagascar to be with you. He plays Mort."
03:04 "Yeah, he's hilarious in this film. It's really good. And what I love about you is
03:09 that you have the perfect face for animation."
03:11 "Oh, thank you. Thank you very much."
03:14 The comedian goes after Andy Richter before setting his sights on Conan's looks.
03:18 It would all seem mean if it wasn't clearly meant to be a joke.
03:22 "And I love this new look."
03:23 "What new look? You've changed the hair, right?"
03:26 "I don't think I have."
03:27 "Oh, how come?"
03:28 Even the guest's dog isn't off limits, making for some funny one-liners and gross-out comedy
03:34 to finish.
03:35 "I have the heaviest dog. The fattest dog."
03:38 "He's a fat dog."
03:39 "Fat dog. He not only drinks, but he eats from the toilet bowl. This is how fat he is."
03:43 Number seven, the kangaroo incident.
03:46 It's not uncommon for animal experts to bring a little excitement to a talk show.
03:51 In the case of this Late Night with Conan O'Brien segment,
03:54 Jared Miller does all that and then some.
03:57 There's a capuchin monkey and a snake, but a kangaroo comes by to steal the show.
04:01 "That's a good idea. Yeah, yank on his tail."
04:05 "But this is a red kangaroo found in Australia, and actually,
04:08 this is kind of a bad time to bring a kangaroo on because it's mating season."
04:11 Miller mentions that it's mating season and struggles to get a firm hold on the marsupial.
04:16 O'Brien plays up the tension of the moment for big laughs,
04:19 hiding behind his guest at one point.
04:21 "He's trying to kick us."
04:22 "All right."
04:23 "He's what? He's trying to what?"
04:25 "See that really long toe on the end of his foot?"
04:27 "You know what? I know that he's trying to kick us."
04:28 Well, it all plays out with a chaotic energy that could turn to disaster at any minute.
04:34 Thankfully for audiences, nobody in the studio gets seriously hurt,
04:38 so everybody can laugh along like it's no big deal.
04:41 "Jared, the next time you come on, you have to bring a collar that's the right size."
04:45 "Yeah, I think so."
04:46 "Right."
04:48 "Yeah, that was pretty unprofessional."
04:50 Number 6. Steve Martin does a top 10 list.
04:54 No stranger to talk shows, Steve Martin always brings out funny ideas for his
05:00 interviews that deconstruct comedy itself.
05:02 "Oh my God. What a mistake."
05:07 "Wait, wait, wait, Steve, what was that all about?"
05:10 "Oh, that's the bit I'm gonna do on Letterman."
05:12 This time around, he performs a top 10 countdown for Conan O'Brien.
05:16 Pretending like it's one of the host's usual bits,
05:19 Martin carries on without mentioning that it's actually a David Letterman premise.
05:24 O'Brien is unable to stop his guest before he starts the list.
05:27 The clueless performance from the comedy legend is hilarious,
05:31 as the jokes become meta and even feature a cameo from a Paul Schaefer look-alike.
05:36 "Bah!"
05:36 "Buh!"
05:37 "Ha ha ha. That is kooky, man. Ha ha ha."
05:43 "Who the hell is that?"
05:46 "Who the hell?"
05:46 As the segment goes on, audiences quickly realize that the comic is dead set on finishing it with
05:52 complete determination. Martin's focus ends up being one of the subtle details that build out
05:57 a classic skit.
05:58 "The number one, the number one bit is..."
06:02 "Okay, I'm sorry, we're out of time."
06:03 "We're out of time!"
06:07 Number five, Dana Carvey's micro-impressions.
06:12 For this appearance, the Saturday Night Live legend joins Conan O'Brien for a versatile segment.
06:18 "Sean Connery is being asked whether he would like to vacation in Spain, okay? And he just says,
06:24 'Yeah, shh.'"
06:26 He practically turns his time into a stand-up set with enough jokes to fill a full special.
06:31 Carvey reminds everyone of his gift for impressions,
06:35 never missing a beat with a wide variety of celebrity voices.
06:38 These include funny interpretations of everyone from Sean Connery to Bernie Sanders.
06:44 "Bernie Sanders, this is new. Bernie Sanders on the Pirates of the Caribbean ride.
06:47 This is rigged! The whole system is rigged! The pirates aren't real!"
06:52 The beauty of these routines is that the comedian only uses a few words at a time.
06:57 Knowing when to step back and let his guest thrive,
07:00 O'Brien lets the comic perform and provides some hearty laughs in the process.
07:06 "I do Michael Caine in kindergarten."
07:08 "Oh yeah?"
07:08 "It's already funny. Um, why do we have to draw between two lines?"
07:15 Number four, Adam Sandler interrupts Chris Farley.
07:19 Among the brightest comedy stars of the 1990s,
07:22 Chris Farley had a way of lighting up any room.
07:25 This late night with Conan O'Brien appearance helps him do that while
07:29 also capturing the performer at a career high point.
07:32 "Do you think Newt Gingrich is gonna make it? You think he's gonna do a good job,
07:35 you know, as speaker? You think he's gonna go all the way?"
07:37 "Conan, I'm not much of a reader."
07:42 He also fondly mentions an impression of Newt Gingrich
07:46 and reveals his lack of knowledge about real politics.
07:49 After the conversation steers towards his love life,
07:52 Farley tries to woo an audience member.
07:55 "You sure are pretty.
07:56 My name's Chris Farley from Moet and Tanneyboy."
08:03 His comedic timing makes this awkward moment really memorable,
08:07 but there's even more surprises in store.
08:09 Adam Sandler bursts in like a jealous lover,
08:12 prompting some amazing reactions from his counterpart.
08:15 "That's not right, Chris."
08:17 "Adam, it's not what you think. I--"
08:19 "You and all these hot tamales remember this, Chris.
08:23 I saw the skid stains in your underwear."
08:26 It's ultimately a quick skit that's absurd in the best possible way.
08:30 Number three, Conan kills some time.
08:33 "We have no writers and we have an hour show, a one hour show to do every night.
08:37 Well, ladies and gentlemen, we're gonna start by talking about my beard."
08:42 Moments like these make us wish Conan O'Brien was still on late night.
08:46 During the 2007-2008 writer's strike, the host, an adept writer himself,
08:52 sought to highlight how important writers are
08:55 by deliberately letting the show go off the rails.
08:58 "Nothing would end this strike faster.
09:00 The producers, the studio heads would see that,
09:05 'Give the writers whatever they want!
09:07 Make that ass stop dancing!'"
09:10 Both admirable and hysterical, O'Brien decided to showcase something he would do
09:15 during rehearsals. He took off his wedding ring and spun it on his desk.
09:20 Conan gave us a rundown of the stakes at play and the obstacles he had to overcome,
09:26 like a slanted surface, to try to break his record of 41 seconds.
09:31 "I know ring spinning, 41. Pretty good."
09:35 While maybe he didn't win the great wedding ring spinning contest of 2008,
09:40 he somehow warmed our hearts and tickled our funny bones.
09:44 "36 seconds!"
09:46 Number 2. Norm Macdonald roasts Courtney Thorne-Smith
09:55 When Norm Macdonald came on a talk show, there was no telling what he would say or do.
10:00 This made for great television, such as this highlight from 'Late Night with Conan O'Brien'.
10:05 "Can you put the picture up of Carrot Top again just so we can all see him?
10:08 Oh there it is again, yeah. All right, okay."
10:12 "Wait a minute, she left Melrose Place to do a movie with Carrot Top?"
10:16 The comedian uses every opportunity to butt into the interview with his trademark humor.
10:21 He even finds time to bash Courtney Thorne-Smith's career choices.
10:25 "I know what it's gonna be called."
10:27 "Yeah, what's that?"
10:28 "If it's got Carrot Top in it, you know what a good name for it would be?"
10:33 "What's that, Norm?"
10:34 "Box Office Poison."
10:35 The segment also includes him making fun of her movie with the comedian Carrot Top,
10:40 with a moment that ranks among Macdonald's finest one-liners.
10:43 "Chairman of the board."
10:44 "Oh, all right. Do something with that, you freak."
10:48 "I bet the board is spelled B-O-R-E-D."
10:55 O'Brien can't stop the train before it goes off the tracks, and we thank him for it.
11:00 Before we unveil our top pick, here are a few honorable mentions.
11:04 Tom Hanks watches whales.
11:07 After noticing a whale in Conan's backdrop, Hanks gets a huge splash of water.
11:11 "That was amazing."
11:21 Bob Saget talks full house.
11:24 The actor revealed that he liked to prank fans of the sitcom.
11:27 "Is Michelle doing okay?"
11:28 "I don't know, Danny. I got problems. DJ didn't come back, and the kid just, like,
11:35 messes himself. He doesn't know what... He's like, 'Oh my God, Full House is real!'"
11:38 Matthew Perry's hockey joke.
11:41 The Friends actor shares fun anecdotes regarding his native Canada and hockey.
11:46 "You have to love hockey if you're from Canada."
11:48 "It's like a rule."
11:49 "Born with skates on."
11:50 "Yes."
11:51 "Very painful for the mother."
11:52 "Yeah, yeah, wow. Very painful."
11:55 Will Ferrell shaves Conan's beard.
11:58 In a comedic rage, Ferrell takes off the host's beard in a hilarious segment.
12:03 "It's all going in my mouth, for God's sake! What the hell? Have you ever done...
12:07 Have you... Do you have any expertise at this? Have you ever done anything like this before?"
12:11 "I've only shaved dogs before."
12:13 Sophie Turner slaps Conan.
12:16 The host tries out a crazy drinking game that includes slaps.
12:20 "How much time do I get? Just go?"
12:23 "Not much time."
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12:45 1. Paul Rudd's Prank
12:49 This might be the longest-running prank in talk show history. At the very least,
12:54 it's one of the funniest gags in the history of Conan O'Brien's television career.
12:58 "Didn't see it going that way."
12:59 "There's a lot of surprises in the last episode. It was pretty emotional. I mean,
13:04 as you can see, Matthew Perry was in a wheelchair for the last episode."
13:09 Paul Rudd's guest spots almost always include a moment for him to show off his latest film.
13:14 Instead of promoting the movie, he plays a clip from the E.T. rip-off "Mac and Me."
13:19 "You've been showing that stupid clip on my show for, I think, 15 years.
13:24 It's from a movie called 'Mac and Me.'"
13:28 It's such a ridiculous scene that it always gets a laugh, no matter how many times it plays.
13:33 Rudd's dedication to the bit never ceases to impress after all these years,
13:38 turning a funny premise into a legendary piece of O'Brien's legacy.
13:42 "So you can see why it bombed."
13:46 "I didn't think whoever dies first, you have to do that at the other one's funeral."
13:50 Did we forget one of your favorite Conan moments? Let us know in the comments.
13:55 "I never really imagined 20 years ago that here we would be."
14:00 Do you agree with our picks? Check out this other recent clip from Ms. Mojo,
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14:08 [Music]