What If I Was?

Michael Penn asked me out tonight.

I don’t have a ton of heroes. You know all about Mr. Rogers. The rest of them are musical: Michael Stipe, Jeff Tweedy, Aimee Mann and Michael Penn. One of the perks of my day job is the opportunity to meet some of them. I’m drawn to these opportunities like an insect to a spotlight. But the truth is, I’m equally reticent.

I have a rule that I never visit a venue until I perform there. It’s totally ego, like I have to enter, say, Sin-e or Arlene or Rockwood as a performer, not a spectator. It’s the same reason I try to always carry a guitar pick in my pocket. I know I’m not a full-time singer/songwriter, but it’s my form of reinforcing that denial. Similarly, my approach to meeting my musical heroes. I used to (heck, I still do) dream of performing with Michael Stipe, or recording with Aimee Mann, or hanging out with Michael Penn as peers. Not as a writer (or worse, an executive) from MTV, but as a musician. So far, that hasn’t really happened, and the likelihood is diminishing with age.

Nonetheless, I was thrilled when I heard Michael Penn had a new record, “Mr. Hollywood Jr,” coming out in August. I jumped at the opportunity to get my hands on the advance, to interview him, and catch his performance. But when it came time to commit to meeting him for the interview, I balked. I opted for a phoner instead. True, I was hard pressed to sneak out of the office in the middle of the day. But the bottom line is that, like anyone else, I turn into a fawning fanboy. And it ain’t pretty.

The interview went well. Michael was pacing outside Joe’s Pub in the East Village. He was fresh from soundcheck. “How’d it go?” I asked.

“Well as can be, I guess,” he said. “You know it’ll sound completely different with a few hundred people absorbing the sound and me pulling on the strings nervously.”

“C’mon, after all these years, you still get nervous?”

“Absolutely,” he answered. “Performing doesn’t come naturally for me.”

I was disarmed in under a minute. Performing doesn’t come naturally to Michael Penn? A guy I’ve seen perform a half dozen times, each time flawlessly? His songs are everything Britney Spears isn’t: smart, substantive, sensitive. He’s a PBS mind in an MTV world. And he gets nervous to boot?

Michael went on to disarm — and reassure — me throughout the evening. His performance was breathtaking, but not just because his songs are brilliant, sing-a-long novellas, his lyrics are deep and clever, he has a pitch-perfect voice, and is a spot-on guitarist. No, more than that. He calls his music “folk music.” He closes his eyes when he sings. He tunes meticulously between songs. He banters awkwardly. And he pauses before beginning every song to gather his wits. So admirable. So amazing. So like me. (The awkward and nervous parts, not the brilliant and amazing parts.)

Michael wrestled with Sony Music for years when he failed to produce a follow up hit to “No Myth.” He was so entrenched in legal mumbo-jumbo that he didn’t even own his domain name. Until just last year, Sony owned www.michaelpenn.com. So, of course, when I heard he was back (he was never far: he scored PT Anderson’s “Hard Eight” and “Boogie Nights,” produced Liz Phair’s album, married America’s Alternative Singer/Songwriter Sweetheart, Aimee Mann, and toured extensively with her), I jumped on his site to see what was up.

Seems that in addition to working on a new album that was somehow steeped in the year 1947, he’d taken some intellectual refuge in a museum called The Museum of the Jurassic Technology. So, you know, I’m a journalist: I inquire. And he says, “I hate to ruin it for you. It’s an extraordinary place. You really should see it for yourself. In fact,” Michael Penn says to me, “Next time you’re in L.A. I’ll take you.” And I’m like, “Michael, be careful what you offer. I’ll take you up on that in a heartbeat.”

So after the show tonight, I walk backstage with his publicist, Mary, to say hello. In fact, I met him once before way back in 1996 when he was touring behind, “Resigned.” Still, I shake his hand and say, “Nice to meet you.” He’s a little distracted, a little scattered. But I don’t blame him. I can’t focus when I walk off stage, let alone when I know I have to go on again in an hour (he performed two sets tonight). And there’s a little bit of a dog and pony thing that goes on with publicists and journalists. Still I had three goals: say thanks, get a photo, and remind him of our date.

So we’re in his dressing room. There are a few few plates of picked over pasta and salad lying about. There’s a pack of American Spirits is on the counter. And I say, “great set,” and we discuss his use of an IFP (in-ear monitor). And I hand him my CD. “Listen,” I say, “I just want you to know that what you do has ramifications. And this CD is one of them. You’re one of the reasons I do this.” And for the first time all night he smiles. And we take an awkward photo. And I remind him, “Next time I’m in L.A…”

“You’re on,” he says.

And I walk out of Joe’s Pub into the New York City night smiling, and singing.

“What if she’s just looking for someone to dance with?”