Zeroing in on 30, rocker Jen Trynin gave herself an ultimatum: either make it now or get out of the game.
Her youthful looks belied the years she spent slogging through the Boston music scene without much to show for it besides too many hangovers. Having graduated from what she called the "Sunday-through-Wednesday-night-folk/acoustic-chick-band wasteland" to the edgier world of indie rock, Trynin decided it was time for her dues paying to start paying off. Either that or grow up, get a real job and, in the process, mollify her Jewish parents, a lawyer and a psychologist, respectively.
And then a funny thing happened on the way to obscurity. Trynin's musical talent -- and an attitude as snarly as her Gibson guitar -- intersected with the female singer-songwriter zeitgeist of the early '90s, precipitating a bidding war for her among major labels. At the dawn of the Lilith Fair era, the Oberlin College creative writing and philosophy graduate suddenly found herself courted by industry titans such as David Geffen and Danny Goldberg, former manager of her heroes Nirvana.
For a brief moment, Trynin was the Next Big Thing. And then it was all over.
"I was the big signing that year, and my record company tried to make me successful as quickly as possible," she said in a phone interview from her suburban Boston home. "But nobody thought about what would happen if it didn't work."
Now older, wiser and happier, Trynin has drawn on her experiences to pen a moving memoir devoid of bitterness but filled with hard-nosed truths about the music industry. Leavened with wit and written with the sharp observations that characterized her best lyrics, "Everything I'm Cracked Up to Be: A Rock & Roll Fairy Tale" (Harcourt) is a heartbreaking account of her journey through what she calls "the belly of the beast." Stitched together with the help of old journal entries and phone messages saved on her answering machine, Trynin's memoir possesses a near cinematic quality that captures the stench of the smoky, beer-stained clubs she often played and the rollercoaster ride that was her career.
And before the fall, there was the ascent.
In 1994, Trynin self-released "Cockamamie," a pop-tinged album that generated a tidal wave of interest among music industry execs hungry to land a promising female artist. The frenzy to sign her grew even more desperate when the suits realized they were competing against one another. Suddenly, managers, entertainment lawyers and music label presidents, who, just months earlier, had refused her calls, materialized at gigs with big smiles and bigger promises.
"Hello, Jennifer Trynin. You should go with us because we're small or we're big or we have other successful acts just like you or we don't have any other acts like you," Trynin writes of life at the height of Tryninmania. "We're the best, best, best and I know you must be hearing this all the time, but I'm sincere, I'm genuine, I get it: your record/voice/songs/real deal/special/substance."
Labels put her up in four-star hotels; flew her first-class, and flattered her like a prom queen. At Mercury Records, an exec handed her a bat and encouraged her to take a whack at a piñata hanging from a light fixture. When Trynin did, large gumballs emblazoned with, "Jennifer Come With Us," fell to the ground. Geffen told her that she reminded him of Linda Ronstadt.
And then there was the Goldberg seduction. After praising "Cockamamie," the then-chief executive of Warner Bros. Records told her that he missed the personal connection he had with Nirvana's lead singer, the late Kurt Cobain: "I was just thinking how if you go with Warner Bros., that maybe I'd have a chance to have another relationship like I had with Kurt, you know."
Those magical words, combined with a generous deal that netted her a nearly $1 million advance for three records, persuaded Trynin to go with Warner Bros.
Given her newfound buzz in the rock world, her overbearing-but-loving Jewish mother stopped hinting that she had wasted her life by not working at Goldman Sachs or The New York Times or by teaching at Harvard. Trynin also felt a certain amount of pride in finally getting to the big leagues.
But Trynin felt less than exhilarated. What if she lacked the energy or talent to truly make it? What if the journey to the major labels turned out to be more meaningful than the arrival?
Trynin's misgivings would prove prescient. Warner Bros. head Goldberg left soon after her signing, leaving Trynin without her biggest and most powerful booster. Soon thereafter, she found herself on an endless tour of faceless clubs in faceless cities, subsisting on booze, cigarettes, junk food and an ill-fated affair with her hipper-than-thou bassist. At every stop, a long-lost boyfriend or friend or friend of a friend wanted to reminisce about the good old days, wanted a piece of her.
As a Jewish woman trained to speak her mind, Trynin alienated some Warner Bros. execs by questioning their marketing and advertising strategies, and by her refusal to play nice-nice with them or anyone. The wear and tear of her nomadic existence on the road to nowhere made her even crankier. When a persistent fan encroached on her space, she whipped out a pen and surprised him by signing his nose. (She later learned that her unwitting victim was a DJ.) During a visit with a clueless disc jockey who vanished after spinning her quasi hit, "Better Than Nothing," Trynin rebelled against the inanity of it all by interviewing herself, playing the dual roles of DJ and Jen Trynin.
"So Jen, about how long do you think we're supposed to be doing this solo interview thing?"
"Not very often," I said, craning my head around hoping that someone, somewhere in the station, might actually be listening to the broadcast and come help me out. "In fact, it's getting a little spooky in here."
"Is it?" I said. "How so?"
"Well," I said, "I'm feeling a little like I'm in the end of that movie "Westworld," like this station is run by machines who just look like human beings and they're all short-circuiting somewhere out in the back, and any minute now Yul Brynner is going to come crashing through that plate-glass window and kill me."
Trynin's shenanigans didn't endear her to her record company. None of that would have mattered, though, if "Cockamamie" had gone platinum or at least gold. But the album stalled, despite Warner's marketing muscle, a slew of gushing reviews and the imprimatur of taste-maker Rolling Stone, which, touted "Cockamamie" as Hot Debut in its Hot Summer issue. Ticket sales for her concerts fell off, and a planned European tour never materialized. Just a year after her much ballyhooed arrival, the Wall Street Journal used her as an example of new overpaid, over-hyped artists who failed to deliver.
After a much-needed break and reassessment of priorities, Trynin laid off the booze and cigarettes and recorded a second album. "Gun Shy, Trigger Happy," like her first effort, garnered stellar reviews, with Entertainment Weekly picking it as the No. 2 Record of the Year, behind U2's "Pop." Unlike the first time around, Trynin dropped her attitude and made nice. But 1997 wasn't 1994; her time had passed. When Warner Bros. declined to release to radio the single, "Writing Notes," a personal favorite, Trynin finally realized her bosses had moved on to the Next Big Thing. Her records, like her career, would soon languish in the bargain bin.
So dispirited, burned out and disillusioned did she become that she accepted a buyout to not record her contractually guaranteed third album. Two years would pass before she picked up a guitar again.
What went wrong? Well, superstar Alanis Morissette burst onto the scene around the same time as Trynin. Signed to a Warner Bros. subsidiary label, her success diverted away attention and sales. Trynin also said the company's marketing approach veered from selling her as a sensitive singer-songwriter to a tough-as-nails rocker chick, sending consumers a confusing and muddled message.
But she also looks inward for an explanation.
"To be a rock star, you just really have to believe you're the [stuff], even if late at night you have doubts," she said. "You need super confidence to the point of narcissism. Although I'm incredibly self-involved, I don't cross that line. If you don't, you're just an artist."
Trynin has since reclaimed her life. She took courses at Harvard Extension, got married, penned her memoir, which, she said, allowed her to "neutralize the past." She also joined a local band, singing back-up vocals and playing rhythm guitar. Music became fun again.
Three years ago, Trynin gave birth to a baby girl, prompting her to re-examine her Jewish roots. Although married to a non-practicing Catholic, Trynin is considering raising her daughter Jewish. Unlike other faiths, Judaism is "not fake and false. There are no silly bunnies," she said, adding that the religion's bedrock values, including its emphasis on questioning authority, also appeal to her.
Trynin said she has few regrets. She would even make the same choices, because they led her to her current contented place. Still, Trynin misses imagining a future rich with rock-'n'-roll fantasies.
"The loudest silence of all is the absence of my old daydream, the one where I used to picture myself in the future, sauntering through the streets of some city, freewheeling, beautiful, unafraid," she writes. "What I miss most is no longer having the dreamy vision of myself floating somewhere on the horizon. Because the truth is, once my future finally arrived, I was still just me - a little nervous, kind of plain, always preparing for the worst."