1. History of Rap w/ Justin Timberlake
Jimmy Fallon has said he has the greatest job in the world. When he first took over for Conan O’Brien on Late Night, it didn’t appear so. He was awkward, laughed too much at his own jokes, and often seemed a bit too starstruck with his guests (his first interview with Robert DeNiro is painful to watch). As he gets ready to take over The Tonight Show, it’s segments like his serialized “History of Rap” which show how he has grown the talk show format into a catch-all of out-of-character fun for his guests and viewers.
2. Carly Rae Jepsen featuring The Roots
One of Fallon’s best assets is his house band and venerable hip-hop artists The Roots — which, fate permitting, will follow him to The Tonight Show. Combine that with Fallon’s sheer love of having guests do what they do best, and you get this charming, catchy redux of last year’s summer hit.
3. Yes, charades can still be fun
Fallon likes to take his guests far from their comfort zone, and what better way to do that than with severely awkward party games. Along with Beer Pong, Password, and Pictionary, Fallon recognizes the inherent joy of watching people be stupid and combines it with the inherent joy of watching famous people be stupid.
4. The Doors Sing the Reading Rainbow Theme
While his Neil Young version of pop songs tends to get more credit, his Jim Morrison impression is all the more impressive not just for its likeness but Fallon’s actual tenor. Combine that with a leather-legging strut and Levar Burton’s soothing lyrics for greatness.
5. Florence Welch Sings “Balls In Your Mouth”
One of Jimmy Fallon’s greatest talents is getting serious artists to divulge in absolute silliness. The dramatic turns of Florence + The Machine make for a perfect fit to Fallon’s sophomoric dirty song.
6. The Leader Of The Free World Slow Jams The News
Watching this, it’s hard to decide had the more difficult job of keeping a straight face: Barack Obama or Jimmy Fallon. Either way, POTUS does a legendary job filling in for perennial Late Night guest Brian Williams, and even manages a few digs at the GOP during an election year.
7. The Cast of 30 Rock For An Entire Episode
30 Rock was a legend in its own right, and Jimmy Fallon’s friendship with Tina Fey (going back to the Weekend Update days) makes this one of his best interviews. It’s the hallmark of a good host to be able to have fun just talking (it is a talk show after all), and there are few better examples than this hour long sit-down.
8. Bill Cosby Takes Jimmy Fallon to South Philly
The Roots have two decades behind them as Philly icons, placing them a distant second behind Bill Cosby. Cosby’s been acting as if he were 75 years old his entire comedic career, and how he actually is. His skepticism against The Roots for their….roots becomes a hilarious and impromptu bit.
9. Nickelodeon-Style Game Shows
Ranging from the impossible to win (“Name That Guy”) to requiring actual talent (“Battle Of The Instant Bands”), Fallon has a litany of game shows with audience volunteers. Perhaps none reminds us of the Double Dare days more than “Models And Buckets”, a messier version of Deal Or No Deal.
10. Jimmy Fallon Is Thankful
Jimmy Fallon’s weekly show of gratitude is an easy comedy set-up, a writing prompt he can keep going for the rest of his career. The segment has also bred two books and some fantastic mugging from Roots keyboardist James Poyser
Bonus: Jay Leno And Jimmy Fallon Sing “Tonight”