Aimee Mann:

First guitar: An acoustic guitar one of her brothers got for Christmas but never played. She was 12.
“I got sick from mono and was home from school for three weeks, and you know mono just makes you completely exhausted. So I got the guitar out and taught myself to play in bed.”

First time she felt her mortality: About 10 years ago, in a car crash.
“We were on tour, and the van got hit by a drunk driver and we flipped over several times. You think you’re gonna die. I developed a real debilitating fear of flying. I just started constantly thinking about what was survivable and what wasn’t. I was terrified to drive over bridges and stuff. That lasted a few years.”

First time she felt like she’d made it: When ’Til Tuesday went on its first tour in 1985—an arena tour with Hall & Oates.
“We were playing in 10,000-seat places. But we were driving ourselves in vans and sleeping two in a bed at Motel 6. We had no money at all. The disparity of playing in arenas and being dirt poor was just weird.”

First thing she’d do if she couldn’t play music anymore: Become a cartoonist.
“I’ve been approached to write a book, and they suggested I do a graphic novel because I really love graphic novels. And I thought, ‘Well, that’s quite a learning curve.’ But I do have a friend who’s a great graphic novelist who lives two blocks away. So we started meeting for coffee, and he started teaching me some stuff. My plan over the next couple of years is to do a graphic novel, like a memoir.”

First time she felt completely happy: As a child spending summers at Cape Hatteras, N.C.
“There were these sort of sand dunes that, for miles, were deserted. I would spend time alone there, and I loved it. I really love the ocean and the sand. Things with my family were like—I grew up with three boys, and there was a lot of tension in the family. So being alone was the happiest I ever was.”