Last night, John Mayer stopped by Jimmy Kimmel Live! where he chatted about his many varied projects, performed one of his newer songs for the studio audience, and delivered a mini outdoor performance that featured a reverent rendition of The Grateful Dead‘s “Fire on the Mountain”.

The impetus for Mayer’s appearance was to promote his new Instagram show. Mayer has long had a large and engaged presence on the platform thanks to his near-constant, rambling, often-bizarre stories and live feeds that seem endearingly more interested in amusing him than the 3.5M people who follow him. With the recent launch of Instagram TV, Mayer is expanding his off-kilter Instagram presence onto the new platform. You can watch the trailer for Mayer’s new IGTV show below:

John Mayer Instagram TV Show Trailer

[Video: Jimmy Kimmel Live]

While the whole thing seems pretty strange to pretty much everybody, it of course makes perfect sense to Mayer, who has built a unique career out of doing a bunch of very different things. As he joked to Kimmel, he admires oddball entertainment Rennaissance man Bill Murray and aspires to be the Bill Murray of music [Note to John: Bill Murray is already the Bill Murray of music, but we get what you mean].

Mayer chatted with Jimmy Kimmel about his diverse portfolio of projects, from his own highly successful solo work to his gig with Dead & Company. “As soon as I heard the music and fell in love with it, I was like ‘I gotta play with these guys,'” he mused. “That’s how nervy I am. Most people would say ‘this is nice, I want to listen to this more.’ I go, ‘get me in that band.'” Kimmel responded, “What John Stamos is to the Beach Boys, you are to the Dead.” Mayer fired back in step, prompting big laughs: “I do not mind the comparison. I would like to be what John Stamos is to all things.”

Mayer also spoke about his duo performances with master comic Dave Chappelle. At the shows, the two entertainers both sing songs and tell jokes, giving them each a chance to try their hand at the other’s craft—buoyed by their long-running friendship and the charismatic chemistry it affords them. As John jokes:

Advice to anyone who’s struggling as a stand-up comic, one of the best things that you can do is just stand next to Dave Chappelle onstage. If you get the opportunity. He’s better at what he does than anybody is at anything they do. That’s why you go see Dave. He’s a great comic, but you’re also watching someone just nail something. … All I have to do is say two funny things and people walk out going “those guys were hilarious!” …

As much as I wanna be a comic, I get a couple jokes in. And then he wants to be a singer, and he’ll sing a couple songs. He’ll sing “Creep”… and I bet you think its the TLC “Creep”, but it’s the Radiohead “Creep”.

He goes on to marvel at Dave’s ability to command a crowd, even when singing, telling a story about watching Chappelle softly start singing Prince‘s “1999” only to have the entire audience singing along with the track’s famous synth lines by the time he hit the chorus. “He’s one of the greatest leaders of a room I’ve ever seen,” Mayer explains. Check out the segment below:

John Mayer Talks Dead & Company, Bill Murray. Friendship with Dave Chappelle

[Video: Jimmy Kimmel Live]

In addition to chatting with Jimmy and debuting his IGTV trailer, John Mayer also performed a mini-concert in their outdoor space, as is customary for Kimmel’s musical guests. The show only aired a portion of the performance, including his recently released single, “New Light”. The set included a number of his more well-known originals as well as a surprise cover of the Dead’s “Fire on the Mountain”, a nod to his work with Dead & Company. As Mayer said following the cover, “Most of you probably never heard that last song before… but it was played in an effort to bring both families together.” You can watch the “Fire” cover and more footage from Mayer’s Jimmy Kimmel Live! performance below:

John Mayer – “New Light” [Pro-Shot]

John Mayer – “Dear Marie” 

[Video: Dear Marie BR]

John Mayer – “Slow Dancing In A Burning Room”

[Video: Gummy Visuals]

John Mayer – “Fire on the Mountain” [Grateful Dead cover]

[Video: Christina Reeves]