Late Night Comedy Sidekicks and Bandleaders: The Good, The Bad and the Ugly

The Good

Andy Richter

The gold standard. While Paul Shaffer may have been the first to satirize the role of late-night sidekick, Richter has never been afraid to bite the stereotype right in its sycophantic, unctuous can. 

Take this bit where Richter forgets how to be a sidekick after Conan’s show took a summer break. Human Resources is right there to help Andy get back on track, reminding him that “You need to make the host believe in the irrational fantasy that he is the funniest person in the world.”

Unlike other sidekicks whose sole job is to laugh at the host, Richter often gets to sing lead, slinging as many jokes as Conan.  Several episodes have us believing Richter is actually smarter than his boss, even as he’s resigned to the indignity of the sidekick chair.

Geoff Peterson

Geoff Peterson was Craig Ferguson’s skeleton-robot sidekick, which was every bit as awesome as that sounds.

“Initially, I wanted something which represented some kind of deconstructionist contempt for the late-night genre and the idea of a sidekick,” says Ferguson. “But (Geoff voice-actor Josh Thompson) became so good at it, he just became a sidekick.”

Are android cronies the future?  And what do we have to fear from our new late-night overlords? “I've gotten a lot of messages from the Robot Skeleton Army on Twitter, urging me to be careful that Geoff Peterson does not become self-aware and turn on humanity,” says Geoff creator and Mythbusters robot guru Grant Imahara. “I can guarantee you that I've put in place programming to prevent that from happening.”

Paul Shaffer

Although Doc Severinson sometimes filled the Ed role for Johnny when McMahon was on a bender, Paul Shaffer was the first hybrid sidekick-bandleader in late night.

He was also the first to perform in character, a showbiz-loving, jive-talking hepcat who loved nothing more than soaking in the hot tub of celebrity excess. Letterman was initially attracted to Shaffer from his work with BIll Murray in his lounge singer sketches on Saturday Night Live -- his Letterman persona definitely borrowed that vibe. 

It helped that Dave was genuinely amused by Paul. “(Dave) was a guy who could make me laugh, and sometimes I’m able to make him laugh as well, and I think that was the start of the relationship,” Shaffer told Billboard. “He always tells me, ‘If you have anything to say, jump in — you have complete carte blanche.’ How many jobs do you get like that?”

Reggie Watts  

Comedy podcast mainstay and musical genius Reggie Watts lends James Corden more cool than he deserves. While Corden is well known for his love of crooning it up with costars in cars, it’s Watts’ effortless jams that allow the host to occasionally pull off a song worth listening to. It’s even better when Corden just sits it out, like when Watts and Donald Glover pulled this instant classic out of their talented butts. 

Give James credit for engaging Reggie in actual conversation rather than simply looking to him for punchline laughs. Their unexpectedly emotional exchange after the death of George Floyd brought a few moments of heartfelt reality to a show that’s often too goofy and gushing for its own good. 

Give Watts his own show already.

The Bad

Hank Kingsley

You folks see that flashing sign up there? Well, that sign says: Apple sauce. No, no... I'm kiddin', it says: Applause. 

One of the all-time great sitcom characters was undeniably a crappy sidekick. He’ll do a commercial for any crap product that offers him a paycheck, and he’ll often try to worm his endorsements into Larry’s live show. He’s painfully insecure, a petty, mean-spirited bully, and a miserable failure at love. His rotating restaurant has problems with health inspectors. He’s mean to Jon Stewart.

Credit to Jeffrey Tambor that we loved Hank anyway. Hey now.

Kevin Eubanks

As a comic partner for Jay Leno, the perfectly bland Eubanks was one hell of a bandleader. He seemed to be perfect for what Leno wanted in a sidekick -- someone to mindlessly guffaw at his jokes, no matter how lame.

That was something Leno’s first bandleader, Branford Marsalis, was unwilling to do. He quit in part because he didn’t want to pretend to laugh at every one of Leno’s feeble bits. "The job of musical director I found out later was just to kiss the ass of the host,” says Marsalis, “and I ain't no ass kisser."  

Over at Stephen Colbert, Jon Batiste has received similar criticism for having little to contribute to the non-musical stuff other than deferential laughter. 

Fred Armisen 

It’s not so much that Armisen is a crummy sidekick -- it’s that you never know when he’s going to be behind the drum kit.

“Because I know Seth and (show producer) Mike Shoemaker so well, they know where I am and they know what I’m working on,” Armisen told The Wrap.  “I’m like, ‘Well, this month isn’t good, I have to be in Portland' … it really is a dream, that whole thing.”

Yeah, it’s a dream!  While Armisen is probably overqualified to be Seth’s sidekick, the on-again, off-again nature of his appearances makes it feel like Armisen is doing the show a favor when he feels like showing up for work. Hey Fred, go make a fake documentary or something and leave the sidekicking to someone who wants the gig.  

The Ugly

Craig Shoemaker 

Not many people remember that Los Angeles Laker star Magic Johnson once had his own late-night talk show. And certainly fewer people remember that comedian Shoemaker was the sidekick on The Magic Hour -- mostly because he only lasted three days. 

What did Shoemaker do to deserve the canning?  Well, he told the Philadelphia Inquirer that The Magic Hour was embarrassing and “an absolute nightmare.”  That ought to do the trick -- even though by all accounts, the show was embarrassing and an absolute nightmare. 

To make things even weirder? Because Magic Johnson was a much better point guard than he was a stand-up comic, Shoemaker did the opening monologue with Magic himself providing the sidekick chuckles. Well, Shoemaker did three of them.  He was actually removed from the couch during a commercial break on the third episode and that was that.

Regis Philbin 

You can’t fire Regis -- he quits!

Regis was Joey Bishop’s sidekick on Bishop’s failed late-night ABC show in 1967. According to The Hollywood Reporter, Reeg heard network higher-ups pressuring Bishop to replace Philbin for the good of the show.  Not wanting to wait to get canned, Regis resigned -- and walked off during a live taping. 

Letters (supposedly) poured in from fans eager for their Regis fix and Philbin returned a few nights later.  At the time, Joey Bishop told the press that Regis was “like a son to me.”  Thirty years later?  Bishop claimed the entire stunt was Philbin’s ploy to get a raise, labeling him an “ingrate.” He also declared that Regis “gives lots of hope to people who have no talent.”  

Damn, Joey Bishop, that’s cold!

Guillermo Rodriguez 

Jimmy Kimmel’s former head of parking lot security seems to be having fun -- but is it at his own expense?

As Troy Patterson commented in Slate, both Kimmel and Chelsea (Chuy Bravo) Handler relied on small, blue-collar Hispanic men as sidekicks, a fact that “could surely serve as fodder for a 10-page Latino-studies paper.”

Guillermo is vaguely reminiscent of Dave Letterman’s bits with Mujibar and Surajul. Guillermo appears to enjoy the gig (it very likely beats working the parking lot) and Kimmel and Rodriguez clearly have affection for each other -- but the laughs are uncomfortable, all the same.

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Top image: Jackhole Productions