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'The Late Shift 2': Who Should Play Whom?

by Danny Gallagher, posted Feb 15th 2010 11:06AM
News that New York Times reporter Bill Carter is working on a pseudo-sequel to his groundbreaking book The Late Shift' made a smile creep across my face. I haven't yet read the book, but the buzz it caused and the weird stories that came out of it just by word of mouth gave it an aura of mysterious wonder that made the television industry infinitely more fascinating than it already was.

It also spawned a pretty decent made-for-TV HBO movie. Now I don't know what kind of craziness "Round Two" has to offer, but the players involved are definitely going to have all sorts of wild secrets revealed from Carter's work and when it does, HBO is going to want the movie rights. So here's who should play who in this new tragic merry-go-round of television programming hilarity that shall be called 'The Late Shift 2'.

Conan O'Brien: Eric Stoltz

From what we've read so far, Conan's role seems to be of the graceful quitter, the man who jumped on the grenade that no one wanted to go near and saved 'The Tonight Show' from becoming programming shrapnel. The 'Caprica' star could certainly fill the bill. They both have a weird gentle quality of seemingly general nice guys, something that Stoltz could easily tap into when the cameras start rolling. Plus, they both have pale skin and a shock of red hair, so imagine the money the production could save on hair dye and face pancake.

Andy Richter: Patton Oswalt

Andy is the loveable pudgy sidekick with a quick wit, some might say quicker than the man in the host chair and the only man who could fill those shoes are Patton Oswalt and, of course, Andy Richter. Hey, he's an actor and he's got mouths to feed too. Oswalt could give the role an interesting dramatic turn, given his recent work in films like 'Ratatouille' and the indie dark comedy 'Big Fan.' He's also a friend of the show and a seasoned road comic who probably knows more about what goes on behind a talk show than the hosts do.

Jay Leno: Daniel Roebuck

When it came to finding a good replacement for Jay (other than the actual Conan O'Brien, of course), the 'Lost' actor who played Jay in the original 'Late Shift' movie just stood out above the rest. His take on the large chinned one felt less like an attempt of doing a bad impression of the man and more of a sincere character study of a guy caught between the ringer of the Hollywood machine and the loyalty of the people who got him into the machine in the first place. The new chapter of the 'Late Shift' story may take on a different twist, but who better to study the character of a man who has aged and weather himself through such a high profile career than the same man who is aging along with him? Plus, I'm sure he still has the prosthetic chin on display in his home or kept locked away in a memory chest somewhere.

Jeff Gaspin: Jon Hamm

The president of NBC's Entertainment division struck me as a company guy who still wants the best for everyone involved and Hamm could fit that role well. Sure it's a sign that he's been typecast as the square office drone supervisor who tows the company line while trying to keep his private life from ripping at the seams, but given 'Mad Men's' popularity and extreme critical acclaim, that's not a bad place to start. And playing the head of NBC's Entertainment isn't a bad place to go either, as much of a final step to hell as that sounds.

Gavin Palone: Sacha Baron Cohen

Conan's agent might not be the Helen Kushnick type that got Jay his 'Tonight Show' throne by playing hardball with a spiked bat, but the hip super-agent stills has a weird tenacity that makes him a fierce negotiator and a shrewd business dude. The man who turned 'Borat' and 'Bruno' into household names and annoying office impressions could draw on that same wavelength with his ability to push buttons and charm in between eye blinks. Plus, if the actual story behind 'The Late Shift 2' somehow involves references to third-world nations and inappropriate dildos, Cohen's agent should already been on the phone.

Jeff Zucker: Tom Arnold

As much as we might like to see the Zuckster turned into some kind of drooling clown who sits behind a million dollar desk and makes animals out of paper clips while his network burns, it still wouldn't be fair to the story, the people involved and the man. Arnold might not be on Oscar's nominee radar but he's actually gotten a bit better as evidenced by his small role as a sleazy porn producer on last season's 'Sons of Anarchy.' He may even be level-headed enough to bring the character some depth but also just a bit untamed to give the man who brought his network the biggest late night disaster since Jack Paar's "water closet" joke just enough crazy to be believable. As for the "drooling bit," I'll leave that up to the producers.

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Rosie O' Donnell has just signed on to play the part of Andy Richter.

February 16 2010 at 5:23 PM Report abuse rate up rate down Reply

Kimmel should play Leno. That impersonation he did when he did the entire show as Jay was evisceratingly perfect. I like Joel McHale for Conan -- he'd need hair extensions, but he has the height and the high-revolution comedy sensibility. Patton Oswalt as Andy would be the best casting in the history of casting. Peter Dinklage as Zucker.

February 16 2010 at 1:22 PM Report abuse rate up rate down Reply
Taylor Costello

They REALLY need to cast Tilda Swinton as Conan. Cate Blanchett played Bob Dylan, so why can't Swinton play Conan?

February 16 2010 at 11:38 AM Report abuse rate up rate down Reply

Maybe for the end of the movie, Rich Little or Dana Carvey could play Johnny Carson looking down from Heaven and saying "Boy, those jerks never learn!"

February 15 2010 at 8:36 PM Report abuse rate up rate down Reply
Jake Levine

Conans not doing anything... Maybe he can play himelf?

February 15 2010 at 12:06 PM Report abuse rate up rate down Reply

Let's hope that if the do a Late Shift 2 that the characterizations aren't quite as cartoonish as they were in the original.

February 15 2010 at 11:55 AM Report abuse rate up rate down Reply

I have 2 changes I'd make to your list and a new character to add.
Jeff Zucker: The guy who plays David Wallace on The Office. Give him a baldness and BOOM Jeff Zucker. Also the Suck It theme song he made sounds like a song Zucker would make about Conan.
Conan O'Brien: Tilda Swinton. Its who Conan wants and she even said she would be glad to do it.
David Letterman: Kevin Spacey. Anyone see this as a good idea besides me?

Now cue the Leno interns to spam the page... NOW!

February 15 2010 at 11:16 AM Report abuse rate up rate down Reply
2 replies to ac's comment

Thank you ac. I was wondering why Dave wasn't on the list. He didn't have a major role in the disaster this time, but I am sure he probably spoke with Conan once or twice. They could also metion the Late Show commericial as the latest stop on the Jay Leno Image Rehabilitation Tour, which is becoming a significant part of this story.

February 15 2010 at 12:22 PM Report abuse rate up rate down Reply

If they're going with the Rehabilitation Tour as part of the plotline, maybe they could get Queen Latifah to play Oprah.

Good call with Patton - if Andy can't play himself, he's the guy for the job.

I definitely agree Letterman ought to be portrayed. Not only is he a survivor of the first "incident", but became a major player in this one with his commentary and the commercial.

There ought to be room for Craig Ferguson and Jimmy Kimmel cameos - Craig for his anti-NBC snark over current goings-on and Jimmy for using his secondary career as a Jay Leno impersonator to comment on the situation.

February 15 2010 at 5:05 PM Report abuse rate up rate down Reply

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