Poor scores on her SAT's--which, DeRogatis reported, she took while stoned--frustrated her hopes of attending college. Therefore, she headed for New York, arriving there "during a weird transitional period in 1978," as she put it in her Capricorn bio. "I didn't know anyone or where anything was happening, so I just hung around at open-mike nights or out-of-the-way comedy clubs and bars. My first musical job was singing harmonies for Pat Benatar."

And it was behind Benatar, who became a pop superstar over the next several years, that she found herself providing "whoa-hoos," as she told Brett Milano of the Boston Phoenix, in a reggae version of Led Zeppelin's classic rock anthem "Stairway to Heaven." Straw admitted to Milano that she "felt a little funky about that, because I wasn't sure it was the right way to do that song. She'd be up there with her leather spandex sequined outfits. And I was the back-up chick in the washed-out jeans, standing there going 'whoa-hoo.'" More dignified work followed, notably a collaboration with pop innovator Van Dyke Parks, who has been a longtime supporter of Straw's. But it was making the acquaintance of cutting-edge drummer and bandleader Anton Fier that set the course for much of her work during the 1980s. Fier led the collective known as the Golden Palominos, a rotating crew of artists from all ends of the pop world eager for a collaborative, experimental side project. Straw sang on two of the group's albums, providing distinctive lead work and backing up such guest Palominos as ex-Cream bassist Jack Bruce, R.E.M.'s Michael Stipe, and acclaimed singer-songwriters Matthew Sweet and T-Bone Burnett. "The coolest thing that came out of my time with the Palominos was a desire to begin writing my own songs," she related in her Capricorn bio. "For the first time, I started thinking of myself as a writer, and not just an interpreter."

Straw worked steadily as a background singer, and has appeared on recordings by Richard Thompson, Rickie Lee Jones, Phranc, Leo Kottke, Evan Dando, and many others. At last, in 1989, she released a solo recording for Virgin Records. The album, Surprise, featured an all-star supporting cast, including Stipe, Thompson, Parks, John Doe of X, Marshall Crenshaw, Dave Alvin, Daniel Lanois, Ry Cooder, and Palomino alums Fier, Jody Harris and Bernie Worrell. Recorded over a year in a variety of studios, the album was, Straw joked to DeRogatis, "an excuse to travel all over the world and visit people, and I called it a record." Critics were kinder to the mix of collaboratve originals and well-chosen cover tunes on Surprise-- Ray Rogers of Interview called it "dazzling," and Entertainment Weekly's Tony Scherman dubbed it a "first-rate debut"--but it sold poorly. Bill Wyman, a columnist for the Internet music site Addicted to Noise, described Straw's debut as "one of the buried classics of the pre-Alternative era."

Hoping to compensate for this disappointment with her next record, Straw asked producers to work with her, but found the process rather lengthy. Virgin, concerned about another potential commercial failure, began to convey what the singer characterized to Wyman as "ideas that didn't have anything to do with the record I wanted to make." She eventually left the label, focusing on guest spots and the occasional acting job. She appeared in the PBS miniseries Tales of the City, and appeared as the math teacher, Miss Fingerwood, on the acclaimed kids' program The Adventures of Pete and Pete. "That was a nice job," she recollected of the latter in her interview with DeRogatis, "because the producers said to the director, 'For the role of the math teacher, we want someone just like Syd Straw.' I didn't even have to audition, which is my favorite way to win work."

Straw then entered a difficult period. She continued to write songs without a record deal, the advantage of which, she told the Los Angeles Times, was that "You can just do whatever you want. It's kind of fun." Yet without a contract, she was unable to make her own records. She also experienced a short-lived marriage in Athens, Georgia. But a new relationship and relocation to Chicago lifted Straw's spirits. She eventually decided to make a record with the Missouri band Skeletons, whose accompaniment brought just the right energy to her compositions. "It's a record that I spent six years thinking about and just about a month to make," she said in her record company bio.
The result was War and Peace, which was released by Capricorn in 1996. Straw, who had continued to enjoy the admiration of critics, earned some glowing notices for the album. David Okamoto of the Dallas Morning News hailed it as "a resilient country-rock concept album about doomed relationships and their caustic, but ultimately cathartic, aftershocks." Entertainment Weekly reviewer Scherman called it "proof of what she can accomplish when she focuses. The melodies lilt, the band rocks, and Straw's reedy voice is an addictive blend of country warmth and urban jitters."

While her admittedly quirky singing and songwriting did not catapult her to superstardom, Straw summarized her awareness of her strengths to Boston Phoenix writer Milano. "Hell, I can tell a story, you know?" she said. "I am trying to be emphatic and empathic and direct and absorbing as I can possibly imagine being." Whatever her fate commercially, Straw seemed guaranteed of a rapt audience for whatever stories she chose to tell.

Discography:
-Surprise (1989)
-War and Peace (1996)
-Live at the Triple Crown (2001) (with The Adventures Of...)
-Whole Wide World (2005)
-Pink Velour (2008)