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In 1995, during his junior year of high school, Bass received a call from Justin Timberlake and his mother, Lynn Harless, who asked Bass if he would be interested in auditioning for the pop group NSYNC after the group's original bass singer, Jason Galasso, had quit.

Along with increasing fame and recognition in the United States the band also experienced a highly publicized legal battle with Pearlman, due to what the group believed were illicit business practices on his part.

NSYNC sued Pearlman and his record company, Trans Continental, for defrauding the group of more than 50% of their earnings, rather than his original promise of only receiving one-sixth of the profits. Today, I’m really happy, and Justin and I are really great friends. And I understand what he was going through, and it was as hard for him as it was for any of us." Vowing to keep the company "a strictly family-run operation," Bass employed his parents and sister as talent scouts, and recruited childhood friend and aspiring country singer Meredith Edwards for the company's first release.

I don't think it's wrong, I'm not devastated going through this.

I'm more liberated and happy than I've been my whole life. Bass's announcement received a large amount of media attention.

There had been considerable media speculation about his orientation due to numerous paparazzi snapshots of him at gay bars and nightclubs, most notably during the preceding Independence Day weekend in Provincetown, Massachusetts.

The thing is, I'm not ashamed – that's the one thing I want to say.Bass dated actress Danielle Fishel of TV's Boy Meets World throughout 19.In his autobiography, Bass documents two gay relationships that predated media speculation; one with a Miami, Florida, native named Jesse, with whom Bass lived for two years, and another with an Idaho native named Joe.Bass later said that he felt the film's success was greatly hindered by its release date, which came one week after the World Trade Center attacks of September 11, 2001.In his 2007 autobiography, Bass wrote, "That was it – our film was finished...once the country went to war, there was no way our film was going to be on anyone's top-priority list." Bass made an appearance in the 2008 film Tropic Thunder.

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