A Britney Spears comeback is the kind of opportunity that has music-industry executives seeing dollar signs. But Ms. Spears, who has spent years battling for control over her life, has given few signs that she is ready to return to the stage or recording studio anytime soon.

The question of what Ms. Spears wants hangs over a hearing scheduled Wednesday, where a probate court will weigh the pop superstar’s petition to remove her father from the unusual conservatorship that has ruled her personal life and finances for the past...

A Britney Spears comeback is the kind of opportunity that has music-industry executives seeing dollar signs. But Ms. Spears, who has spent years battling for control over her life, has given few signs that she is ready to return to the stage or recording studio anytime soon.

The question of what Ms. Spears wants hangs over a hearing scheduled Wednesday, where a probate court will weigh the pop superstar’s petition to remove her father from the unusual conservatorship that has ruled her personal life and finances for the past 13 years. That court-approved legal arrangement, which governs everything from her daily moves to whether she can marry, has led to a public outcry that has, in turn, fueled renewed interest in the future of Ms. Spears’s career.

The conservatorship fight between Ms. Spears and her father, James P. Spears, has made the singer a symbol of women’s empowerment, one capable of attracting casual fans who might have ignored her previous nostalgia-fueled shows, music-business executives say.

Britney Spears’s debut album ‘…Baby One More Time’ drops in 1999. It has sold over 14 million copies in the U.S., according to the Recording Industry Association of America.

Photo: BERNARD WEIL/Toronto Star/ZUMA PRESS

“The iron couldn’t be hotter to announce something,” says John Kellogg, an entertainment lawyer and program director for the Master of Arts in Music Business at Berklee College of Music’s online school. “Nobody has gotten this amount of publicity in quite a while.”

Wednesday’s hearing is expected to be a turning point for Ms. Spears. Even if the conservatorship persists for some time longer, she would likely have more control over her activities and $60 million fortune with Mr. Spears out of the picture. Mr. Spears, who had said he would step down at some point from the conservatorship, filed a petition to end it earlier this month.

With more control, there are questions about Ms. Spears’s next career move. Even a limited return would be a music-industry milestone: Ms. Spears, a RCA Records artist, is one of the bestselling stars ever, having sold 33.8 million albums in the U.S., according to Billboard, fifth-most among female artists since 1991.

Some of her recent comments appear to leave the door open for live performances eventually.

Ms. Spears’s song ‘Toxic,’ from her fourth studio album, 2003’s ‘In the Zone,’ becomes a Top 10 hit. It is now her most popular song on U.S. streaming services, with 565 million streams, according to MRC Data.

Photo: Gerald Herbert/Associated Press

“I’m not gonna be performing on any stages anytime soon with my dad handling what I wear, say, do or think,” according to a post on her Instagram account in July.

Yet Ms. Spears, who turns 40 in December, has also described feeling pressured to perform in the past and wanting to have a third child, according to her remarks before the probate court in June. On Instagram that same month, a post stated that she had no idea whether she will return to performing.

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Larry Rudolph, Ms. Spears’s longtime manager, resigned in July, saying in a letter to the conservatorship that he had become “aware that Britney had been voicing her intention to officially retire.” Ms. Spears has yet to replace him, industry executives say.

Ms. Spears’s legal team didn’t make her available for an interview. Mathew Rosengart, her new lawyer, and Creative Artists Agency, her talent agency, declined to comment. Business manager Michael Kane and publicist Jeff Raymond didn’t respond to requests. James P. Spears’s legal team didn’t respond to requests.

Ms. Spears also recently became engaged to boyfriend Sam Asghari, according to her Instagram account. Her finances, which include cash assets of $2.7 million and noncash assets valued at more than $57 million, have improved since her conservatorship began in 2008, according to court filings.

The pop star’s conservatorship begins in February 2008, led largely by her father, James P. Spears—following a series of widely publicized struggles with mental-health issues. At the time, Ms. Spears acknowledges its necessity.

Photo: Damian Dovarganes/ASSOCIATED PRESS

The star has hit the brakes on a return before. In early 2019, she scrapped a planned Las Vegas residency, announcing an indefinite hiatus and citing her father’s health issues. That was “not the real reason behind it,” a music executive with knowledge of her decision-making says. “She [pulled] the plug because she literally couldn’t do it,” the executive says.

“I said, ‘I don’t wanna do [the residency]’ … I was getting really nervous,” Ms. Spears told a Los Angeles court in June about the 2019 show. “It was like lifting literally 200 pounds off of me when they said I don’t have to do the show anymore because it was really, really hard on myself and it was too much. I couldn’t take it anymore.”

Performance issues have cropped up in the past. In 2013, for example, the Los Angeles Times criticized her previous “Piece of Me” residency at the Planet Hollywood Resort and Casino in Las Vegas, saying the star’s “presence felt so diminished.”

Older listeners associate Ms. Spears with early hits like “Oops!…I Did It Again.” Her debut 1999 album “…Baby One More Time” has sold over 14 million copies in the U.S., according to the Recording Industry Association of America.

Ms. Spears’s Las Vegas residency, ‘Piece of Me,’ begins its lucrative four-year run in late 2013.

Photo: VW Pics/ZUMA PRESS

Later generations also have embraced the singer. While recent album sales haven’t matched her early highs, her midcareer and latest albums are unusually popular on streaming services for a veteran act. Ms. Spears has 12 songs with more than 100 million U.S. streams each that span the breadth of her career, according to MRC Data.

Music critics have come around, too. Ms. Spears’s latest album, 2016’s “Glory,” is her second best-reviewed album, according to review aggregator Metacritic. That appeal helped her “Piece of Me” residency, which ran from 2013 to 2017, to gross nearly $140 million, according to Billboard.

Las Vegas talent prices have risen in recent years, industry executives say. A residency makes more sense than a full-blown tour for Ms. Spears, since it allows performers a more normal lifestyle, Mr. Kellogg says.

Whether Ms. Spears will return to the recording studio is also unclear.

Ms. Spears remains in contract with RCA Records, and owes more music to the label, according to the music executive with knowledge of her decision-making. If she didn’t wish to record, she could negotiate an exit from her contract. Barring that, RCA would be wise to wait for Ms. Spears to make a move, rather than pressuring her, says Zach Scott Gainous, a Nashville-based entertainment attorney and artist manager. “Do they really want to be that villain?” he says. RCA declined to comment. RCA reissued “Glory” with additional tracks in 2020.

After years of staying mostly silent about the conservatorship in public, Ms. Spears rails against it in a court hearing in June, calling it abusive and informally asking for it to end. She petitions for the court overseeing the case to remove her father as conservator of her finances.

Photo: Chris Pizzello/Associated Press

Should Ms. Spears retire publicly from performing and recording, she could do what many stars have done—unretire down the road, Mr. Gainous says. “It’s more likely she does something in the long run than nothing at all ever,” he says.

“I’ve worked my whole life,” Ms. Spears told the court in June. “I deserve to have a two- to three-year break and just, you know, do what I want to do.”

Write to Neil Shah at neil.shah@wsj.com