Bruce Springsteen has never been much of a jokester, so it was a shock to see him dressed up like his 1975 self singing Willow Smith's "Whip My Hair" with Fallon's hysterical Neil Young character. Fallon says that the real Neil Young has a standing offer to come onto the show.
Paul Simon's 1980 classic "Late In The Evening" was thoroughly funkified when The Roots played it with him in the summer of 2009. He was one of the first classic rockers to see the value of playing on Late Night; many have, of course, followed his lead.
The SNL skit that put YouTube on the map and gave birth to countless viral videos was revived when Chris Parnell stopped by Late Night in March 2009. Andy Samberg popped up behind the couch to go "way back to 2005" and The Roots provided amazing old-school hip-hop beats and backing vocals.
The Roots and Yacht Rock captain Christopher Cross seem like an absurd combination, but their performance of "Ride Like The Wind" with surprise guest Michael McDonald could be the greatest performance in the brief history of Late Night. Who knew that Cross could play guitar like that? They nearly topped themselves the following year when Robbie Dupree came on to sing "Steal Away."
Weird Al's 1988 super obscurity "Good Old Days" was a childhood favorite of Jimmy Fallon's, who requested the track when Al stopped by the studio. Yankovic was game, and the Roots found a hidden funkiness in the song that nobody could've anticipated.
Most talk shows feature artists plugging their newest songs, but Late Night has always encouraged them to reach into their catalogs. When The Beasties stopped by in the summer of 2009 they did an incredible version of "So What'cha Want" with The Roots. It was one of their final performances before taking a break when Adam Yauch discovered he had cancer.
All Beatles fans know that the lyrics to "Yesterday" originally referred to scrambled eggs. Fallon and his writers decided to write an entire song about breakfast food to the tune of "Yesterday," and McCartney agreed to sing it — but only if Fallon sang it with him.
A year before Paul McCartney came on Late Night, Ringo Starr stopped by to challenge ?uestlove to a drum-off. You can see the shock on everybody's face when as the Beatle holds his own (despite playing a mini-kit) on the Roots cut "Here I Come."