The above video is from a Counting Crows show in 1999. Sometime during the performance, a young Jimmy Fallon was called on stage to perform some parodies of famous 90s bands centered on a very 90s object, the troll doll. If the combination of this doll and the bands that were famous in 1999 makes you feel old, well, sorry. That’s real.

What’s pretty amazing about this video is that Jimmy’s spoofs are extremely on point, and musically, he really holds his own. You can see it in the way he commits to the style of each musician he’s mimicking—put simply, he appears to be very talented. But when you take a step back at his whole professional career since 1999, this initially seems a bit strange. As a Saturday Night Live cast member from 1999-2004, Fallon—nah, let’s go back to Jimmy—built a reputation for himself as the guy who couldn’t keep his shit together and constantly broke character during his funnier cast mates’ best moments.

Naturally, this became a running joke of its own, and we somehow came to appreciate Jimmy for his absolute lack of an ability to stifle laughter and keep the illusion of a scene together. Check out this classic sketch from 2001, set at the fictional Welshly Arms Hotel. Anyone with a Best of Will Ferrel DVD tucked away in a box somewhere will recognize the skit as, not surprisingly, one of Ferrel’s finer moments on the show. In it, he and Rachel Dratch portray two sexually charged “luvahs” with ambiguous accents, getting cozy in a hotel hot tub with Jimmy’s weary traveler, Dave. It only takes about 20 seconds for Jimmy to crack his first smile, and less than halfway through he’s already bursting with laughter. This is a hilarious sketch on its own merits, but it really hits its apex when all of the actors are struggling to keep their composure. Jimmy is obviously the reason why all of this begins in the first place.

Part of what makes the best comedians so good at what they do is their ability to keep a straight face in even the most absurd moments. Jimmy is notoriously bad at this, and it begs the question—has he really ever been a good comedian? In another great SNL skit famous for the complete breakdown of all its actors, the first ever Debbie Downer bit features Jimmy, Amy Poehler, Fred Armisen, Horatio Sanz, Kenan Thompson, and host Lindsay Lohan. As soon as Thompson introduces himself as “Billiam,” Jimmy shares a knowing look with Dratch, and it’s all downhill from there.

Now, this isn’t meant to belittle Jimmy’s presence on SNL. The fact is he had many great moments, and many great characters, like his version of Barry Gibb in The Barry Gibb Talk Show. In most cases, when he was the center of a skit, he excelled with any kind of musical accompaniment. It didn’t have to be a full blown music video, but when given the chance to sing, play guitar, impersonate a known musician, or all three, he was far better than he was as a straight character balancing out his dynamic cast mates in pure dialogue sketches.

Last week, Jimmy took the reins from Jay Leno on The Tonight Show, after five years as the host of Late Night With Jimmy Fallon. Plenty of time has been spent trying to figure out what the new Tonight Show will be like with Jimmy at its center, but if he and the writers know what they’re doing, they’ll stick to what worked for Jimmy on Late Night. His best bits as a talk show host have, by far, been musical acts, and he’s always benefited from the talent of The Roots, who can turn on a dime with Jimmy’s improvisational kinks. Check out this slow jam with none other than Barack himself:


You really can’t go wrong in a skit like this. The Roots deliver a great beat, and all Jimmy has to do is keep his timing in check. For him, that’s easy. Of course, the star power of the POTUS doesn’t hurt.

One of Jimmy’s longtime collaborators and friends, Justin Timberlake, has also helped Jimmy’s musical inclination shine throughout the years. On Late Night, JT appeared several times, the most notable of which featured him and Jimmy teaming up for segments of The History of Rap. In fact, during the first week of the Tonight Show with Jimmy as host, JT showed up for the fifth edition of the act:


This is really as good as it gets for Jimmy. He’s got an incredibly talented band in The Roots backing him up, and an A-list singer by his side. Granted, anybody in the world could probably make something happen with that supporting cast, but it really all comes together with Jimmy’s comedic sensibilities in music. Everything from his voice, to his timing, to his body language, makes the skit what it is. He and everyone around him have smartly realized where his talents come out the most, and try to make them shine whenever possible.

So knowing all of this, when it comes down to it, is Jimmy Fallon a musical comedian, or a comic musician? He’s definitely not great at being purely a comedian, but it’s also pretty clear that he couldn’t really make it out there as just a musician either. Jimmy seems to be the rare case that falls squarely in the middle. He has enough of both to make himself shine, and more importantly, the ability to push his limitations to the background. Giving him one of these labels isn’t worth it because it doesn’t matter—he’s good at what he does, and as perplexing as that is, we all know it’s true.