The shock jock is the latest personality to weigh in on the public's mounting concerns for the pop star in the wake of the release of the "Framing Britney Spears" documentary and her ongoing conservatorship battle with her father, Jamie Spears.
"I think I'm Free Britney now, I think I'm full on Free Britney," Stern said on his Sirius XM radio show to his co-host Robin Quivers via Variety.
Stern was referring to the growing #FreeBritney movement. Supporters of the movement believe Jamie is not only suppressing his daughter via the conservatorship, but many have also questioned whether her father is skimming money from the singer's fortune for himself.
According to the report, Stern on Wednesday analyzed Spears' ability to be in charge of her finances and other areas of her life. While he questioned if she is, in fact, capable of assuming the responsibilties, he turned to other stars like Charlie Sheen, Gary Busey, Kanye West and Shia LaBeouf for comparison.
"Ozzy [Osbourne] bit the head off of a bat in a business meeting," Stern pointed out. "He's in charge of his own finances."
Stern has made headlines in the past for jokes about Spears. When the singer signed on as a judge of "The X Factor" in 2012 with a reported $15 million contract, he questioned her abilities and said he planned to "tune in to see what kind of train wreck she is."
"I think it’s a wonderful decision, Britney still thinks the Earth is flat," Stern said. "Listen, I think we’re going to tune in to see her, if she can sort of function through the thing."
Stern went on to say he anticipated Spears wouldn't bring any real substance to the competition show.
"As far as any real criticism, I think Simon [Cowell] and L.A. Reid will be doing that. I think Britney is going to stand there and eat a lollipop and wear a sexy outfit. I don’t anticipate great opinions out of her," he continued.
"I think she’s going to sit there like J.Lo and [say], ‘Oh, you’re wonderful. You’re terrific. Do you think I could get a perfume endorsement out of this? You think I could perform on the show?’ I think that’s what it’s about," he added.
Also, in 2003, Stern's interview with Limp Bizkit's Fred Durst about his rumored romance with Spears went viral. When the radio personality asked Durst to detail the seriousness of their alleged relationship, Durst replied, "Ain’t it funny scared to admit it/ Very first night made the Limp dog hit it," citing his own lyrics.
The "Framing Britney Spears" doc has brought renewed attention to the downfalls of the singer's superstardom. The New York Times program led fans of the star to speak out against Justin Timberlake and Diane Sawyer for the way they treated the pop star in the past.
Last week, Timberlake issued an apology to Spears and Janet Jackson amid fallout he's received.
"I specifically want to apologize to Britney Spears and Janet Jackson both individually, because I care for and respect these women and I know I failed. I also feel compelled to respond, in part, because everyone involved deserves better and most importantly, because this is a larger conversation that I wholeheartedly want to be part of and grow from…," Timberlake’s statement read in part.
Actress Valerie Bertinelli and "The View" co-host Meghan McCain are just a couple of numerous stars who've spoken out about the documentary in support of Spears.
Meanwhile, live performances have been scarce for the singer in recent years, as her lawyer alleged last year in court that she won't perform as long as her father, Jamie, has control.
Jamie, who has denied all rumors about himself, fought last year to have the details about the case sealed. The famous father even spoke out about the movement, calling it a "joke."