Ironically, David Bowie’s first #1 single in the US was “Fame,” a funked-up framing of the demands, disappointments, disillusionment and even depression that often – perhaps inevitably – result when an artist is tossed into the gears of that soulless hit-making machine called the music industry.
And though Jen Trynin was only 11 when that track topped the charts in 1975, by her early 30s she could have very easily written the lyrics by herself, based on her own stinging brush with pop-star celebrity and critic’s darling-level acclaim.
A power-poppin’ melody maven whose self-released 1994 album sparked a major-label bidding war for the ages, Trynin also could have penned the lyrics to another famous song from ‘75, Pink Floyd’s “Have a Cigar.” As she details with aplomb in her book Everything I’m Cracked Up to Be (Houghton Mifflin Harcourt, 2006) – a chronicle of her rocky professional and personal roller-coaster ride after signing with Warner Bros. in 1995 – few can identify quite as well as she can with empty assurances like “you’re gonna go far,” “you’re gonna fly high,” “you’re never gonna die,” “you’re gonna make it if you try” and – that promise of all promises – “they’re gonna love you.”
Trynin has included only original material on her three solo releases (29 songs across one EP and two LPs), but she recorded Harry Nilsson’s “Morning Glory Story” for the tribute album For the Love of Harry: Everybody Sings Nilsson (MusicMasters, 1995).
Born and raised in New Jersey, Trynin grew up with an eclectic variety of music, her attorney father partial to musicals, her psychologist mother drawn to classical and her brother a top-40-rock fan. She started playing piano at age four, began singing at 10 and picked up the guitar at 11, taking singing and guitar lessons intermittently throughout her childhood.
Trynin cites her earliest six-string influences as James Taylor, Joni Mitchell, Bonnie Raitt and Neil Young. She wrote her first tune at age 11 – “The Lonely Seagull,” she still recalls a full 47 years later – and says her biggest songwriting inspirations when she was young were Taylor, Mitchell, Young, Paul McCartney (both with The Beatles and solo) and Elton John.
During high school, where her favorite subjects were English and math, she played in a few rock bands with classmates, was in the photography club and played field hockey. After graduating in 1982, she enrolled at Oberlin College in Ohio and majored in creative writing, with minors in philosophy and electronic music. In her senior year, she fronted a rock group.
Move to Boston, Early Area Gigs
In 1987, Trynin graduated from Oberlin and moved to Boston’s Jamaica Plain neighborhood, where she lived until 1999. She had planned to move to Chicago to be a dramaturgist (“a script doctor for plays among other things,” she says) but the theater where she was going to work lost its funding, so she chose Boston instead since she had some friends in the area.
For the next seven years, Trynin juggled several jobs – running a small desktop publishing business from her apartment, working part time for The Boston Parents Paper (then a Jamaica Plain-based monthly) and waiting tables at Doyle’s Café in Jamaica Plain (alongside Rick Berlin) – while performing at coffeehouses and other small venues like T.T. the Bear’s Place and The Middle East in Cambridge and Toad’s Place in New Haven as part of what she’s called “the Sunday-through-Wednesday-night folk/acoustic-chick-band wasteland.” She says her favorite spot to try out new songs was the now-shuttered Green Street Station in Jamaica Plain, where (pre-Dave Grohl) Nirvana, one of her favorite bands, played in July 1989.
In 1988, Trynin cut her first record, the five-song EP Trespassing, in New York at RPM Studios (where ‘Til Tuesday recorded their debut LP in 1985) with a band that included bassist Mark White, later of Spin Doctors. Released by Pathfinder Records, three songs saw modest local radio play, “Venus & Me,” “I Could Move Mountains” and “Daddy’s Happy Now,” but she left a decidedly deeper impression in the alt-rock/indie-pop cement six years later.
In 1994, Trynin released her first full album, the 11-track, electric-guitar-centric, hook-heavy Cockamamie, on her own label, Squint Records, after recording it at Q Division Studios in Somerville with producer Mike Denneen (whom she married in 2000), a Yale graduate who co-founded the studio and joined the Berklee faculty in 2011.
After the track “Better Than Nothing” saw significant airplay on alt-rock stations across the US and critics began comparing her exceptional songwriting skills to those of fellow Boston transplant Aimee Mann (who contributed backing vocals to one song on the album, “Snow”), Trynin found herself in an entirely unexpected role – the pop-music marketing machine’s latest version of “new and improved” – with record-company executives including David Geffen (who told her she reminded him of Linda Ronstadt) and Danny Goldberg (Warner Bros.’ then-CEO, Led Zeppelin’s former publicist and Nirvana’s one-time manager) luring her toward their respective labels.
“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,” Trynin writes in Everything I’m Cracked Up to Be about the wooing she received, echoing an hilariously satirical “Have a Cigar” lyric, “The band is just fantastic, that is really what I think. Oh, by the way, which one’s ‘Pink’?” Once, when she arrived at Mercury Records for discussions, an A&R exec handed her a bat and told her to whack a piñata hanging nearby; when she did, hundreds of gumballs fell to the floor, each one emblazoned with “Jennifer, Come With Us!”
Warner Bros. Signing
After multiple meetings with label bigwigs, for which record companies flew her first class and put her up in five-star hotels as part of the courting process, Trynin went with Warner Bros. Goldberg told her that he hoped they could establish the same kind of “close personal connection” he said he’d had with Nirvana’s Kurt Cobain and gave Trynin a three-album deal – plus a nearly $1-million advance – to bring her on board.
Cockamamie Reissue, Tour
In 1995, Warner Bros. reissued Cockamamie and “Better Than Nothing” hit #15 in the Billboard Modern Rock Tracks Chart, #40 in the Billboard Mainstream Rock Tracks chart and #89 in Australia, but the LP peaked at #74 in the Billboard 200 and the follow-up single failed to chart.
Despite a raft of rhapsodic reviews and the LP being name a “Hot Debut” in Rolling Stone’s “Hot Summer” issue, both album and ticket sales fell dramatically below Warner Bros.’ targets and the label put a planned European tour on ice. Limited promotional support left Trynin playing at small venues across the US including at the Rathskellar, House of Blues and Avalon in Boston, where she performed as part of a US tour with Buffalo Tom in September following an appearance on Late Night with Conan O’Brian in July. One of her favorite things that year, she says, was when “Happier,” the opening track on Cockamamie, was featured in an episode of the MTV series Beavis and Butt-Head.
The Alanis Factor
By the spring of 1996, Trynin’s blink-of-an-eye stint as the apple of Warner Bros.’ execs’ eyes was coming to a close, with Goldberg, her biggest champion at the label, having left for Mercury and the company concentrating its promotional power on a singer-songwriter 10 years her junior, Alanis Morrisette, whose Jagged Little Pill album on Warner Bros. sublabel Maverick hit #1 in the US and UK that year. “I loved ‘You Oughta Know’!” Trynin said in March 2023, referring to the smash single from the Morrissette disc.
Gun Shy, Trigger Happy
In 1997, Warner Bros. issued Trynin’s sophomore LP, Gun Shy, Trigger Happy, under the name Jen Trynin (not Jennifer as on Cockamamie). Also recorded at Q Division, the album was a far more polished effort in terms of production than its predecessor even though Trynin had written all 13 tracks in bare-bones style on an acoustic guitar in her living room.
While the album was a commercial nonevent by any measure, critical acclaim was effusive with Billboard praising it as “strikingly lovely,” Rolling Stone saying it achieved “a perfect balance between wry chutzpah and forthright tenderness,” People calling it “one of 1997’s strongest and most mature discs” and Entertainment Weekly putting it at #2 in its Albums of the Year list (behind U2’s Pop).
Leaving Warner Bros.
When Warner Bros. refused to accept Trynin’s recommendation that the LP’s first single be “Writing Notes” – insisting on “February” instead and renaming the song “Getaway” since it would be released in the summer – she realized that the label’s decision makers had moved on from her to whatever they thought the next “next big thing’” would be, particularly after the label didn’t even bother to release the “Getaway” video.
Looking back, she thinks switching from “Jennifer” on the cover of her first album to “Jen” on her second “didn’t help my music career,” she said in March 2023. “I did it just because pretty much everybody called me ‘Jen,’ not ‘Jennifer,’ but I had no idea – and no music-biz people alerted me to the fact – that doing that might really confuse my already not-huge audience.”
Burned out and “pretty bummed out,” she says, Trynin accepted a buyout from Warner Bros. that freed her of all contractual obligations to record a third album. And she didn’t pick up a guitar for the next two years.
Loveless, Band of Their Own, The Cujo
From 1999 to 2003, she played guitar and sang backups in the Boston-based indie-rock quartet Loveless. The band recorded one LP, 2003’s Gift to the World, which received critical acclaim from a number of publications including The Boston Globe, Rolling Stone and Spin, and their single “Go” was included in an online campaign for clothiers Abercrombie & Fitch.
In 2015, after 12 years out of the public eye while she and Denneen raised their daughter, Trynin joined the all-female rock septet Band of Their Own, which played in and around Boston and included Kay Hanley of Letters to Cleo and Tanya Donelly of Throwing Muses, Belly and The Breeders.
In 2018, as a tribute to Denneen, who passed away that year, Trynin and their daughter performed a song he’d produced for Fountains of Wayne, “Stacy’s Mom,” at the Paradise Rock Club with Letters to Cleo.
Since 2014, Trynin’s been part of a four-piece outfit called The Cujo, which she classifies as “lawncore.” In June 2023, their seven-song debut EP, Songs from the Suburbs, was made available on the digital distribution site Bandcamp.
Death is a Number, EARFULL Series
Trynin is writing her second book, tentatively titled Death is a Number, and some songs to accompany it. In July 2023, the literary quarterly Ploughshares published an excerpt (“Hello Kitty”) in its summer edition.
For the past several years, Trynin has co-hosted EARFULL, a performance series that features writers and musicians and holds events about once a month at the Burren Irish Pub and Restaurant in Somerville’s Davis Square and summer shows at the Branch Line Restaurant Patio and Pavilion in Watertown. Past guests have included Bill Janovitz of Buffalo Tom, David Minehan of The Neighborhoods, Kay Hanley, Tanya Donelly, Howie Day, Damon and Naomi, Duke Levine and Mason Daring.
Comments on Warner Bros. Experience
Talking about her Warner Bros. experience with The Boston Globe in 2006, Trynin said she came out of the whirlwind “scarred but smarter,” stressing that the experience provided her with invaluable knowledge that she probably couldn’t have gained any other way. “I learned a whole lot,” she said. “Not just about the music business, but about myself and what I really want. And I was kind of surprised by what I want, because it’s not what I thought it was.”
(by D.S. Monahan)