But now, amid tabloid scrutiny over his changing appearance, the former Olympian (with his altered appearance) is standing front and center.
Jenner, 64, has been open about undergoing plastic surgery in the past, beginning with a partial face-lift and nose job in the mid-'80s, a "botched" procedure that took a toll on the athlete's self-esteem.
"If you Google my name, the worst plastic surgeries of all time or whatever it is … they've compared me to Michael Jackson," he said on an episode of Keeping Up with the Kardashians.
In 2009, Jenner went under the knife for a second time to correct the first operation. The process, featured on an episode of the show, garnered the support of the entire Kardashian clan.
And a satisfied Bruce joked of his new appearance in a 2009 episode: "It doesn't hurt to be mistaken for Brody once in a while. Do you think I'll get carded?"
Despite his family's approval, Jenner faced plenty of media scrutiny for his changing appearance, even feuding with Jimmy Fallon over the talk-show host's harsh jokes about his transformation.
Now, four months after his split from wife Kris, Jenner is sporting a new look, one that's raising eyebrows once again. The dad of 10 (including his four stepchildren) has been growing his hair long, manicuring his nails, and, most controversially, he has allegedly undergone a tracheal shave, flattening his Adam's apple.
Sources close to Jenner categorically deny that he is making any sort of efforts to transition into a woman, despite breathless tabloid claims, and say the reality star is simply happily experimenting with a fresh look. "He has this, 'I may be an old man, but I'm cool and young too' syndrome and no one can tell him otherwise," says a source close to the family.
Beverly Hills plastic surgeon Dr. Toby Mayer, who has not treated Jenner, says that excessive physical change can be a symptom of body dysmorphic disorder, a condition in which a person has an unrealistic view of his or her own appearance.
Says Mayer: "When people have an unusual preoccupation with the way they look, they will never be satisfied. They will always find some flaw on their face that they think [fixing] will restore perfection."
Counters the family source: "Bruce thinks he looks great. He doesn't listen to the criticism."
Reporting by JENNIFER GARCIA and RAHA LEWIS