Aimee Mann, who will be headlining Sunday at the Stern Grove Festival in Golden Gate Park, has every reason to feel that she’s earned her day in the sun, or, as it may be, the fog. The Richmond, Va., native took home her first Grammy this year – albeit for best album packaging – and her concerts are selling out nationwide. Later this month, she’ll be playing Symphony Hall in Boston with the prestigious Boston Pops. Still, she’s no stranger to professional stress.

By now, her quest for independence from major-label tyranny has become something of a cautionary tale for music-industry neophytes. After achieving breakthrough success at a young age with ’Til Tuesday, the ’80s New Wave outfit whose hit single “Voices Carry” became an early MTV staple, Mann’s love affair with her label quickly soured. After the quartet’s two subsequent efforts failed to scale the Billboard charts, Mann went solo. Though her solo debut, 1993’s Whatever, drew near-universal praise from critics and esteemed peers like Elvis Costello, it met with little commercial success.

Her follow-up proved an even more harrowing endeavor. Mann put the finishing touches on I’m With Stupid just as her label filed for bankruptcy in the spring of 1995, delaying its release for the better part of a year. After an abbreviated stint with Reprise Records, she landed with the David Geffen Company, and recorded her most accomplished album to date, the brilliant Bachelor No. 2. The result? A one-way ticket to music-industry purgatory. Citing the lack of an obvious single, Geffen released Mann from her contract but retained the rights to her music, holding Bachelor hostage. Only the intervention of filmmaker Paul Thomas Anderson, who made Mann’s music the focal point of 1999’s Magnolia, enabled her to buy back her work.

Today, Mann, 45, runs her own record label, SuperEgo, and has released three more critically acclaimed records, including 2005’s The Forgotten Arm. And though she has admitted that she never wanted to bear such a hefty responsibility, Mann now enjoys the freedom to do whatever she pleases – even releasing a weighty concept album and training in her spare time as an amateur boxer. “To me, it was an interesting idea to take characters and a story and explore them more in-depth rather than just dipping into one song and moving on to something else,” she says. “The ‘Forgotten Arm’ is a boxing move, and the idea is to keep punching with one hand so that your opponent forgets to defend the other. It’s a metaphor for the album’s underlying story, this character having a drug problem that nobody takes seriously until it really starts to debilitate him.”

Having witnessed the rise and fall of prog-rock pioneers like Yes and Jethro Tull, Mann knows that the very term “concept album” is all too commonly associated with “pretentious self-indulgence.” But she also knows that The Forgotten Arm would never have seen the light of day without SuperEgo and its parent company, United Musicians, home to Mann, her musician-husband Michael Penn and comedian Patton Oswalt.

“My manager and I were sick of the frustrations that come with being on major labels, from the frustration of having to go through any number of people to get anything done to the fact that the people who ultimately make the decisions change from month to month. You’re never dealing with anything constant. It’s really hard to please so many different people, and it’s depressing to feel that you have to first please some random person who’s not even a music fan, who’s listening to music solely for its commercial potential. You have to deal with too much ignorance.

“When you work, not even considering whether the music is commercial or not, it gives you freedom to be much more creative.”

Clearly, that freedom has paid off, despite the fact that Mann isn’t a fixture on the Top 40. After years of playing to packed houses at the Fillmore, she looks forward to something different at Stern Grove.

“Every show I’ve played in San Francisco has been notably great for me,” she says. “Nothing’s exploded, so that’s good. We tend to sprinkle in a few outdoor festivals every year because people are there more for the hang-out, the picnics and the frisbee games than the music. But I enjoy being in the background, being in that kind of picnic atmosphere. I don’t have to be the center of attention.”

Then again, don’t bet that she won’t be.