One day, a bartender friend at The Viper Room, Shannon, asked him to watch the register while she had a smoke outside. After that he began working there sporadically, urging the elite crowd to cough up bigger tips for his coworkers. Mostly, though, he was delighted to talk to such cool people without having to introduce himself.
“It was what I imagined the Left Bank must have been in the ’20s, with Gertrude Stein and Hemingway and Picasso,” says Duritz, the former Berkeley English major who wrote his college thesis on the astounding avant-garde poet Hilda “H.D.” Doolittle, of the conversations he witnessed. “I was getting chased all over Berkeley, but who gives a fuck about me when Jack Nicholson is walking down the street?”
He might have overestimated his anonymity. As he began to work on new songs, the band would sometimes play the Viper under pseudonyms. One night, while the first season of Friends was airing, Jennifer Aniston came to listen. Their pals conspired, telling each of them that the other had an enormous crush. Their short-lived relationship became tabloid fodder, affirming some popular sentiment that he made music only for money and glory.
“There is nothing more flattering than someone who likes you. I thought, ‘I am popular now, not the geek I was,’” he says. “You get lambasted for selling out for just dating a girl. I have nothing but regrets about it, but I think that’s unfair to say, because it’s not her fault.”
But then, well, he did it again. He’d met Courtney Cox, of course, through Aniston, her Friends co-star. While the band was working on its second album, Cox’s roommate and Duritz’s friend got hit by a car. He was recording at night, so he’d go sit with her in a hospital room until the mid-afternoon. Cox would join him bedside, and they fell into a romance that was barely better than the circumstances of its start, maybe worse.
“It wasn’t the best relationship, at all,” he tells me, frowning. “She was not a nice person, brought up in a really bad Southern household with a lot of really bad examples. We were both deep in our own troubles.” (Cox’s representatives did not respond to a request for comment.)
At least one absolutely perfect thing, though, emerged from that fractious spell: “A Long December.” One night, amid his days of hospital stays, Duritz left the Viper Room late and headed to a friend’s house until four in the morning, eventually driving to his place in Laurel Canyon and heading straight for the piano. By the time the sun appeared, he had written what has become a cross-generational hymn, the last two exhausting years escaping him through one glorious exhalation.
He slept for a few hours, drove to the Geffen offices, and played it for Tony Berg, the band’s new rep there. Berg told him no one wanted to hear “Hollywood” sung that many times, but the band cut it that night anyway, in seven takes and with almost no overdubs. Then Duritz drove to The Viper Room and, after closing, made friends and coworkers sit in his red 1971 Volkswagen Karmann Ghia convertible and listen to the track. “It’s the most perfect song I ever wrote, the only one I never get tired of,” he says. “The moment I wrote it is just crystalline to me somehow.”