There’s no job quite like that of a late night bandleader. Being proficient in every type of music imaginable — from hip hop to K-Pop to Opera — isn’t enough. You also have to be able to land a comedy bit, keep the show moving, and always know when to laugh at the host’s jokes. With Reggie Watts returning to Comedy Bang! Bang! this week to offer Kid Cudi some late night comedy show bandleader tips, here are a few supremely talented musicians being drop dead hysterical.

10. Cleto Escobedo III, Jimmy Kimmel Live!

When Jimmy Kimmel was given the keys to his own late night outpost, his first thought was “how can I get Cleto in on this?” Jimmy and Escobedo had grown up together in Vegas, and he’d always considered his longtime friend to be a musical savant. He was worried that ABC wouldn’t sign off on him picking his unknown, childhood friend as bandleader. Thankfully, after taking some execs to a performance, they immediately agreed. Escobedo has gone on to have a well received career fronting Cleto and the Cletones.

9. Doc Severinsen, The Tonight Show with Johnny Carson

Doc first joined the The Tonight Show in the ’50s, during the Steve Allen era. He wouldn’t become the bandleader until 1967. His outrageous fashion sense soon trumped his incredible trumpet playing, becoming a staple of Carson’s nightly monologues. While never a huge part of the comedy, Severson proved he could be a natural when given the chance.

8. Bobby Rosengarden, The Dick Cavett Show

A one of a kind studio musician, Rosengarden played on The Steve Allen Show, The Ernie Kovacs Show and Johnny Carson’s Tonight Show before being given his own band on The Dick Cavett Show. While he wasn’t known for his comedy chops, Bobby and his band could jump in on virtually any song, at a moment’s notice. And because Cavett created such a casual environment — where musicians, actors and newsmakers could show a different side of themselves — it wasn’t rare to see comedians jump in with the band. Granted, Jerry Lewis’ reputation has taken a hit in the last few years. Maybe there’s a better clip.

Hmmm, Woody might be a bit too controversial too.

Oooookay, maybe we should just move on…

7. Jon Batiste, The Late Show with Stephen Colbert

Colbert has said he chose Batiste as the leader of the Late Show band because he enjoyed improvising with him during his Colbert Report appearance. So far the pair have displayed a natural on-air chemistry, whether it’s in a comedy sketch or while grooving to the funky opening theme music.

6. Max Weinberg, Late Night with Conan O’Brien and The Tonight Show with Conan O’Brien

It’s easy to go down a rabbit hole of classic Max bits from the glory days of Late Night. The drummer for Bruce Springsteen and the E Street Band, Conan gives Max credit for helping the show survive its turbulent, early days. Not a natural comedian, Weinberg carved out a niche for himself by being unfraid to go dark, especially with his sleazy persona. The Max of Late Night fame never met a hooker he didn’t like…at least until they ripped him off.

5. Fred Armisen, Late Night with Seth Meyers

Fred Armisen was a natural to assume the helm of the Late Night band when Seth Meyers took over as host. The duo had long been collaborators and friends on Saturday Night Live. Armisen, who began his career in music, could ably handle the various responsibilities of the job. The only problem is Armisen’s schedule with IFC’s Portlandia and Documentary Now!. (Not that we’re complaining.) Still, Fred has created some memorable moments during his time on Late Night.

4. Questlove, Late Night with Jimmy Fallon and The Tonight Show with Jimmy Fallon

It was quite the coup when Fallon first convinced Questlove and The Roots to be his house band on Late Night. What was a surprise was how adept Questlove proved to be at comedy. Quick with a laugh, he had plenty of personality to provide a counter balance to the show’s antic host. Fallon has excelled at putting his guests in positions where they can be silly and real. The above clip is a perfect example of how that bleeds over to the band as well. Jason Sudeikis was right — when it comes to the North and this video, the Internet never forgets.

3. Paul Shaffer, Late Night w/ David Letterman, The Late Show w/ David Letterman

Paul Shaffer must have been grown in a lab for the express purpose of being a late night bandleader. Few combine the music genius, comedy chops, and outrageous personality of the longtime Letterman sidekick. But Shaffer made a name for himself in the weird nexus of comedy and music long before Letterman came calling. A key part of the Toronto comedy scene that birthed Gilda Radner, Dan Aykroyd and Martin Short, he soon became the keyboard player for Bill Murray’s lounge singer act, an actor in Spinal Tap, a member of the SNL house band and the musical director for none other than The Blues Brothers. It was only a matter of time before he found his way to Late Night and the “World’s Most Dangerous Band.”

2. Reggie Watts, Comedy Bang! Bang!, The Late Late Show with James Corden

Reggie Watts built a career on his unique talent for combining improvisational music genius and downright silliness. As bandleader for Comedy Bang! Bang!, he got to be a much larger part of the action than most musical sidekicks do. While he’s moved on to Corden’s Late Late Show, we’re happy to see him back to his old tricks in his ’80s-themed “How to (Band) Lead” video.

1. Kid Cudi, Comedy Bang! Bang!

Kudi, a rapper first discovered by Kanye West, originally found his fame thanks to a popular mixtape. No one would have suspected his future lay in comedy, but we’re glad he’s chosen Comedy Bang Bang as his new home. Having recently taken over as CBB‘s bandleader and Scott Aukermanck’s musical sidekick, he’s already carving out his own incredible voice, one hilarious song at a time.