Will Jon Stewart — not Conan O’Brien — succeed Jay Leno on ‘Tonight Show’?
- July
- 12
I’ve always preferred North Salem resident David Letterman to Jay Leno. Letterman’s once-groundbreaking alternative approach to late-night comedy bred his most critically acclaimed contemporaries, including Conan O’Brien and Jon Stewart.
I don’t think Jay’s a bad guy or anything—his hilarious “Headlines” segment or one of my favorite A-list guests sometimes will convince me to flip from CBS to NBC for a few minutes—but I’ve always had a far greater fondness for all things Letterman since NBC tabbed Leno for “The Tonight Show.” Still, we Suburbarazzi must have some respect for the late-night ratings champ: After all, while Leno grew up in Andover, Mass., he’s a native of New Rochelle.
Because Leno tends to stay out of the tabloids, the best gossip of late that revolves around “The Tonight Show” involves his eventual replacement. So, for one shining moment, let’s discuss an empty seat on a talk show that doesn’t involve “The View.” (Hooray!)
If Leno sticks to his word and retires when his contract expires in 2009, NBC will be faced with a few options. The right thing to do—on a few levels—would be to hire O’Brien, whose rough start in the mid-’90s has blossomed into improved ratings and late-night’s most consistently funny hour. Not only has NBC announced that the former “Simpsons” writer would take Leno’s post in ‘09, but also O’Brien has the best chance to charm new viewers while retaining devout fans.
But of late, rumors have been circulating that NBC execs are trying to woo Stewart for “The Tonight Show.”
As much as I love Stewart’s insightful interviews, ironic gravitas and impeccable delivery on “The Daily Show,” a shift to network late-night poses a few problems—almost all of which would involve ratings, not a lack of talent. He would probably be asked to strike a happy medium politically, potentially alienating liberal fans of “The Daily Show” and fighting an uphill battle to attract conservative viewers who hate it. Plus, his previous attempt at a late-night show didn’t fare so well.
Also, should NBC pick Stewart over the previously announced O’Brien, it would result in the biggest late-night controversy since Leno unfairly claimed Johnny Carson’s seat over Letterman, potentially prompting a backlash among viewers. (Although it warrants mentioning that O’Brien wouldn’t exactly be walking away empty-handed; his contract buyout has been reported as high as $40 million.)
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I’m not saying the former Bronxville resident was blitzed for a segment on “The Tonight Show.” But thanks to 

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