Tuesday Debate: Is Jay Leno Funnier than Conan O'Brien

By Jake and Glenn

Nothing has happened more shocking in the past few days than the murder of Dr. George Tiller. However, this weekly debate series wasn't created just to debate the hottest issue of the times. Sometimes we have to address the simmering undercurrents of television entertainment, and no dish has been simmering longer than the recently boiled over transition of the Tonight Show from Jay Leno's steady hand to Conan O'Brien's wacky hand. Their comedic styles are as different as their DNA. When Leno took over the Tonight Show from Johnny Carson in 1992, the inevitable comparisons between them surfaced. Last night Conan O'Brien debuted as the host of his new Tonight Show and rather than shy away from the comparisons, we tackle them head on. Is Jay Leno funnier than Conan O'Brien?

Jake: I'll come clean, I'm not what you'd picture when you close your eyes to do a meditation exercise visualizing the ultimate late night talk show fan. That's right, I'm not a huge talk show fan. That being said, I am a fan of Conan O'Brien. I think his characters and bits are usually very funny, his interviews are usually decent and his musical guests are often not bad. Jay Leno, on the other hand, is a dreadful comedian, terrible interview and has bad musical guests (unless you consider Ricky Martin good). Glenn, who is an advocate for both Leno and Ricky Martin will lead you to believe that Leno is the king of late night, and perhaps ratings-wise he is. I have yet to see the new Tonight Show, but I don't need to to know that Conan is better than Jay.

Glenn: Without getting sidetracked, I do want to point that although he hasn't enjoyed success in America since Livin' La Vida Loca, Ricky Martin keeps churning out the hits for his Latin audiences. This is not unlikely Jay Leno who, despite not receiving the "critical" acclaim of people like Conan O'Brien, is one of the hardest working and consistently funny men in show business. You see, even Jay Leno's friends (though we've never met, I include myself in this group) will admit that he's a work horse. He does five comedy shows every week and has since 1992. Conan O'Brien has only done it since 1993. It's almost beneath me to present Tonight Show bits from the past seventeen years as a defense of Leno but we all know and love: the Dancing Itos, Jaywalking, Headlines and anything involving Howie Mandel. I'm not arguing that Conan O'Brien isn't funny at all, but rather that Jay Leno is so popular so he must be doing something right.

Jake: Jay Leno is not funny. His monologues are like death rattles from Auschwitz. I'm not going to stand here and lie to you and tell you that Conan's monologue are great, but O'Brien is not a professional comedian, but Leno is. Neither Leno, nor Conan are a hard-hitting interview, but Conan has the ability to make his guest seem funny. Leno cannot make anything seem funny. I don't understand the decision for him to move to an earlier time slot, but given NBC's desperation it makes sense, I guess. Conan moving to the Tonight Show, which is a smart move. His audience is getting older and has to go to the office in the morning, they need his show so they have something to discuss during their lunch break. Also, as Glenn knows, the Dancing Itos haven't been on Leno since August 13th, 1997.

Glenn: The worst part of living on the East coast, besides everything being expensive, the pervasive rudeness and the emminent threat of a terrorist (by that I mean right-wing domestic terrorist) attack, is that the Tonight Show is on at 11:30. Most people in DC have one to two hour commutes and have to be awake at 5am. If you think these hard working, white Americans are going to stay up until 12:35 to see the musical guest on the Tonight Show, you're insane. But back to Leno. If he's so bad, why was the only time a sitting President has gone on a talk show earlier this year, to be interviewed by Jay Leno? Obviously our PRESIDENT thinks that Leno is a good interviewer, and felt safe enough in his Burbank studio to visit and answer tough questions about the problems facing our country. Kevin Eubanks, who I have not mentioned for fear of the racial undertones Jake will now employ, is the Joe Biden to Jay Leno's Barack Obama. Together they are an unstoppable comedy team. On the last episode this past Friday, Jay heartfeltly thanked Eubanks for being there to help him when jokes bombed, on the rare occasion that they do. As a professional stand-up comedian, Jay knows that not everyone joke will hit but it's about fighting through the bad ones until you socre one about Bill Clinton and Monica Lewinsky. I always liked those.

Jake: Everything about Conan's version of the Tonight is superior to Leno's. Andy Richter is better than Stuttering John. Max Weinberg is better than Kevin Eubanks. I'm sure that Conan is not going to get the calibur of guest that Leno was able to with his softball questions and non-threatening style. Conan is slightly sarcastic and a goofball. Jay Leno is a piece of shit. If I woke up tomorrow as Jay Leno, I'd walk up to Mavis, give her a kiss and then blow my brains out all over my old car collection. I would not want to be that guy for more than 20 minutes. I don't care about his money or his fucking cars. I'd love to be Conan. I know this debate is not about who you'd like to be more. I mean, Leno is old and probably suffers from aches and pains, at the least. Who would want that? I'd find this debate more difficult if we had to discuss who was funnier between Conan and Letterman.

Glenn: Conan is funnier than Letterman. I'm also with you on who I'd rather be. As a tall, reddish haired man of Irish descent, I already feel like O'Brien sometimes. Plus we're both funny! I guess, deep down, I'm arguing Jay Leno is funnier than him because I also think he's funnier than me. That might seem like a ridiculous justification, but it's no less ridiculous than the idea of a bunch of murder trial judges dancing for no particular reason. I've yet to hear you acknowledge how funny some of the Headlines are, but I'm done waiting. I'll acknowledge them on your behalf: they're great! Ultimately we'll never know who is funnier until Conan gets his shot at the Tonight Show for seventeen years. In 2026, I make a vow to return to this website - which at that point will probably be the only site legally allowed on the internet - and acknowledge that Conan O'Brien is funnier. But not a day before.


  1. i had to refresh this page 23 times just to make sure i was reading it correctly. i had yet to meet someone personally who would chose leno over conan in any contest, except that of whom has the bigger chin. i h8 leno and love conan. i love letterman too. i also find them both (conan, letterman) dreamboats.

    p.s. "reddish" hair glenn? really? i think it's safe to say your hair is just red.
    p.p.s gr8 deb8

  2. also why is it we (humans) always say conan's first name and leno and letterman's last names?

  3. to me, glenn arguing for leno over conan is as shocking as glenn arguing for scott roeder over dr. tiller. i can only imagine (and hope) that this was one of those scenarios where you guys put it off until 2 a.m. tuesday morning. you couldn't think of a topic to debate, so you had to settle on one that you were both on the same side of and draw straws to decide who had to debate the obviously wrong side. glenn lost. please tell me this is the case.

    conan is just more unique than o'brien. if we called him o'brien instead of conan, we'd all forget whether we were talking about the talk show host or the drunk irishman passed out at the end of the bar at last call. leno and letterman have more distinguishing last names.

    i always wondered why people called h. clinton hillary during the 08 elections, while all other candidates were known by last names. you could reasonably argue that it's because bill is/was such a prominent figure in politics, but when bush jr ran we all called him bush instead of george, and his daddy was bush too. blatant sexism! gender inequality!

    longest comment ever.

  4. i think that has more to do with how hillary marketed herself, as in "hillary for president" as opposed to "obama for america." but that of course doesn't mean it wasn't a deliberate move to market her as the WOMAN running for president, as opposed to someone running for president who happens to be a woman, which is sexist in a way. but also something she chose.

  5. true, true. i'm not saying that the title was imposed upon her (although i'm not 100% certain of the origins of "hillary 08"...it was probably her people, but could've been the media or even opponents initially??), but i do feel like a male candidate would be less likely to campaign by his first name (except for ol' ike, i guess). sadly, there are reasons why a strong, top-level female candidate would want/need to come across as less "threatening"...and campaigning on first name basis is one way to do that. i don't know.

    go conan! whooo!

  6. i'm with you. hillary's choice probably had something to do with making her less threatening - and on the dark side, they do have sarah palin as sarah, condoleezza rice as condi. but then, as you said, there's ike (eisenhower and missouri's own skelton). rudy guliani campaigned as rudy. fred thompson was fred 08, and mitt romny pretty much favored his first name too. (anyone remember the MittHeads?? cos i don't.) don't get me wrong - i'm usually the first person to call something sexist, but i just don't think it works here.

    gosh, who would have thought we'd have TWO tuesday debates!!

  7. tuesday late night debate!

    i'm not saying that there aren't male candidates who run on a first name basis (obviously, you just listed a handful), but that one of the main motivators behind running as a first name (whether the candidate is male or female) is to repair or manipulate the candidate's image in some way. the official running name is contrived, just like any other aspect of the campaign, to make the candidate seem more "folksy" (ugh -- i never wanted to hear that word again after 08) or less threatening. guiliani obviously had his own image issues and difficulty relating to the constituency. in clinton's case, i would argue that her particular "image issue" was that she was seen from the start as "bitchy," humorless, not feminine enough, etc. ...all traits related to her gender. her choice to run as hillary instead of clinton had a lot to do with disassociating herself from bill, yes, but i would argue that it was also a contrived campaign decision to soften or counter her "bitchy" image. if a male candidate came across as aggressive and confident, he wouldn't have to soften his image.

    i'm not sure why i'm arguing for hillary here. i was for obama from the beginning. i just feel like clinton had some unfair prejudices against her that were gender-based and that contributed to her loss. i feel like the media picked up on clinton's confidence and aggressiveness and spun it in the same way they spun the Dean Yelp of 04, to similar (although not as directly devastating) effect in the polls. i'm not trying to sound like a old guard nutcase here, but i do think there are still subtle (and sometimes not subtle) prejudices against women in politics -- or at least in the upper ranks. i'm sure your mom has her own stories to tell along those lines.

  8. i definitely agree with every once of my body that there is sexism in politics, and hillary was treated unfair - although no less unfair than obama was due to his race - due to her sex (...but i also think there is a stronger case for hillary's campaign showing racism than obama's campaign showing sexism), i just don't see the correlation with the name thing. i think it's just a dumb thing that politicians - both female and male - do to seem more like "the people."

  9. hm, perhaps. i was making the argument up as i went along. we better stop arguing before someone comes along and calls us bitches!



  11. It's just like women to talk about THE MALL!

  12. I live right by the one Iowa's biggest malls (or the biggest data is a bit conflicting at this point) bottomline: Yes women do love malls and it makes for a fabulous place to pick up tail.

    Shopping list:

    Rubber Melons

    Yes, I went there and I said it and I am NOT taking it back.

  13. 1 Let's move this comment debate to next week's official Tuesday debate. There's no law on OYIT about letting females arguing against each other, especially if the topic is related to sexism.

    2 I did what I had to do for the debate. I wanted to address the murder of George Tiller, but Jake didn't want to draw the ire of pro-choice activists.

  14. I just didn't know how to make the George Tiller situation humorous. At the time we debated I didn't want to have to really work to make shit funny.

  15. yeah, there's not really two sides to taht issue...

  16. For me it goes Letterman, Conan, and that's it. Maybe because we only got CBS growing up, but I never watched Leno, and I still can't stand to watch him now.

    What would've been a more interesting debate is Craig Ferguson vs Carson Daly. I've never watched either of their shows so I don't know which is funnier and I would like someone to inform me in debate form.