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]