Blackbird Spyplane: Speaking of rare beauties, I asked you to pick a special possession to talk about, & you landed on a deadstock ‘80s-era varsity jacket (above) you got from David Letterman. You recently posted on IG about your love of Conan — what does Letterman mean to you?
JM: “Any guy who’s had an older brother has grown up around this engine of cool stuff that we couldn’t quite get to: They’re a little older than you, they have their own bedroom, they’re watching things a little bit over your head, picking up on music that’s a little over your head. So my older brother, who’s a genius as far as I’m concerned, got really into Letterman, and watching him watch Letterman, I was watching him get fed.
“Letterman was this trusty depot: 5 nights a week you could hang out in this place where, if you were a bright person — but one who also didn’t want to use their intelligence manipulatively — you could watch someone use their intelligence for entertainment purposes. Basically misappropriate their intelligence! I grew up in Fairfield, Connecticut, and if you grew up in New England and you were bright, there was a good chance you were going to go into some dark art, like become a defense attorney. But Letterman was sending up erudition by misappropriating it for nonsense, and I always found that heroic.
“He made the show into a club for smart kids who didn’t like a**holes, who didn’t like being bullied, who didn’t like this idea that you could use your intelligence to get rich off other people. Here was a guy on TV who wants to see, with his analytical mind, whether a man wearing a velcro suit can stick to a wall.”
Blackbird Spyplane: You got this jacket when you performed during his last-ever week on the air… How did you get yr hands on it?
John Mayer: “So Dave requested that I come on and do ‘American Pie’, and learning that song was kind of my tribute to him: ‘I’m going to consume myself with this for one week, infuse myself with it, and when I do it it’s gonna be just that one time.’ So I told them, Can I do it in a Late Night varsity jacket? Because growing up, I remembered seeing the crew wear them in the bumpers coming back from commercial.
“They found one for me to wear and they were, like, ‘This came out of the boss’s closet’ — or if not the boss, someone around the boss. And when I was done they said, ‘It’s yours to keep.’”
Blackbird Spyplane: Whatta score… peace to WORLDWIDE PANTS INC.!!
JM: “This might have to go under lucite. It’s this beautiful touchstone of an era. And talk about trying to fold time over on itself — I was able to send off Dave wearing a varsity jacket from, like, year one of the NBC show. Whether I’m playing in Dead & Company — this band that started in 1965 — or I’m making a record that pretends I was me now in 1988, this is the joy of my life: I get to travel through time with a guitar.