Over the past few years, Perez Hilton and Britney Spears have shared quite a tumultuous relationship. Hilton, who rose to fame for his celebrity gossip coverage and tabloid photos, has made Spears' perplexing breakdown era circa 2006-2008 as one of his most-talked-about topics. Interestingly, the singer also enlisted Perez Hilton for the opening video for her Circus Tour in 2008, in which he plays Queen Elizabeth I of England.

Related: Here's What Jamie Lynn Spears Has To Say About Britney's Conservatorship And Testimony

However, as the recent #FreeBritney movement sparked online conversations from all over the world, Hilton has somewhat tried to make amends with the singer and has apologized for the troublesome remarks, moving on from his problematic past. Was his apology enough or was the damage he potentially caused too much to overlook over 10 years later? Will Perez Hilton and Britney Spears every truly be on good terms? Here’s a simplified timeline of Perez Hilton and Britney Spears' relationship.

 

11 Perez Hilton Mocked Spears' Addiction Issue & Sold A T-Shirt

During the heyday of the singer's career, Perez Hilton made fun of her addiction issues while calling her an unfit mother and spreading a rumor about a sex tape.

However, that's still nothing compared to what he did shortly after Heath Ledger's sudden death in 2008. He made a shocking remark on his website and sold a t-shirt that says "Why couldn't it have been Britney?" with an image from Brokeback Mountain. Yikes.

10 Labels Sued Him For Using Britney Spears' Songs

In 2007, RCA/Jive Label Group, the label that sheltered the singer, sued Perez Hilton for illegally distributing recordings by the singer on his gossip website. According to the report, the website illegally obtained and posted at least ten completed songs and unfinished demos from the singer's then-upcoming album, Blackout. Ironically, the news broke out as the singer was fighting in court over custody of her two children from her ex-husband, Kevin Federline.

9 'Framing Britney Spears' Was Aired

More than a decade after that, The New York Times aired the Framing Britney Spears documentary that shattered the internet. The 74-minute documentary follows the singer's well-publicized rise to fame as a teenage pop star and her court-mandated conservatorship. Framing Britney Spears aired earlier this year on FX and Hulu to a welcoming response from the fans and critics alike.

Related: 10 Times Britney Spears Nailed The Answers To Totally Inappropriate Interview Questions

8 Perez Showed Regret For His Vile Comments & Defended Journalist Diane Sawyer

Not too long after FX aired the documentary, Perez Hilton revealed that he regrets his vile comments about the singer during the earlier days of his blogging career. Speaking on Good Morning Britain, the blogger says that, "Thankfully, hopefully, many of us get older and wiser."

"I think a lot of people just want to blame this person and that person, and it's not as simple as that," he added. "There are real mental health issues at play with Britney Spears."

7 He Said The Singer Would Be 'Dead' If It Wasn't For Conservatorship

However, he also gave another shocking interview with The Sun and said that the singer would be "dead" if it weren't for the conservatorship.

"If she didn't have a conservatorship in place, I would be concerned that Britney would be dead, truly. There are certain things that I don't agree with though," he said. "If she’s under this conservatorship because she needs to, why should her dad be the one calling the shots and making money off of it?"

6 Spears' Explosive Court Hearing Audio Was Leaked

This summer, Britney Spears' shed more light on her concerning conservatorship state. She detailed a lot of disturbing events that happened in the past few years, including the time where she wasn't allowed to get pregnant and married her current boyfriend.

"I'm not able to get married or have a baby, I have an IUD inside of myself right now so I don't get pregnant. I wanted to take the IUD out so I could start trying to have another baby," Spears told the Wednesday court hearing. "My dad and anyone involved in this conservatorship, including my management … they should be in jail."

5 'I Carry Deep Shame And Regret,' Said The Blogger About His Treatment Of Britney Spears

"I can't say I was just young and dumb," the blogger said in an interview with Kay Burley of Sky News, saying that he's taking "full accountability" for his past behavior.

Related: Britney Spears Fans Disgusted As Reports Of Her Dad’s Alleged Behavior Emerges

"I know I did not express myself as well as I could have. I didn't lead with empathy and compassion, which thankfully seems like most people now are understanding the severity of Britney's situation. I absolutely apologize and carry deep shame and regret," he further added.

4 However, He Won't Remove His Past Remarks On The Singer

Although he has come forward to take accountabiltity for the way he reported on Britney Spears in the past, Perez Hilton also expressed that he will not be removing any of his old blog posts on the pop star.

According to Newsweek, Hilton's site "still hosts posts from 2007, in which he scrawled 'I miss rehab' and 'loser' on her face." In an interview with Newsweek, Perez Hilton explained, "I have removed posts before that celebrities have reached out and said, 'That article caused me pain.' Or their reps have reached out. But, typically, I have left my past awfulness up to speak for itself and serve as a reminder and a warning. I am ashamed of my past but I'm not trying to scrub it from the internet or pretend it never existed."

"If I keep all my old posts up, I'm criticized. If I take them down, I'm criticized. I'm genuinely sorry for my behavior over a decade ago and I think my change and growth is obvious. I know I'm a different and better person today."

3 He Supported #FreeBritney

On another occasion, Hilton has publicly supported the online #FreeBritney movement alongside other problematic characters in her life, like ex-boyfriend Justin Timberlake.

"It's official! #BritneySpears has DEMANDED that her conservatorship end. And that it end NOW. And she's impassioned! Speaking so eloquent about the mistreatment that she claims to have received from her father and her team. Wow. Wow. Wow. #FreeBritney," he tweeted.

2 Fans Don't Take His Support As A Welcoming Response

However, many fans are not having it and think it's a little too late for redemption. Perez Hilton was one of the people in the tabloid culture that contributed to Britney Spears' alarming mental health state in the 2000s. He helped shape the public idea that the singer was unhinged and an unfit mother to her children. Some are left wondering if he had kept his mouth shut, would Jamie Spears be as powerful today?

In addition fans have been quick to point out that despite his apology and regret, Perez Hilton is continuing to cover the Britney Spears drama in a questionable light.

1 Britney Spears Is Reportedly Planning To Retire

After the long-lasting battle, Spears is reportedly thinking of retirement, per her longtime manager Larry Rudolph who'd previously resigned from the position.

"It has been over 2 1/2 years since Britney and I last communicated, at which time she informed me she wanted to take an indefinite work hiatus," he revealed. "Earlier today, I became aware that Britney had been voicing her intention to officially retire."

Next: Celebs Who Have Spoken Out About Being Silenced (Besides Britney Spears)