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Who: Oscar-winning actress Renée Zellweger, 50, and Grammy-nominated country singer Kenny Chesney, 51.
How They Met: The unlikely pair met in January 2005 at NBC’s “Concert of Hope” tsunami aid telethon. Zellweger had hoped to meet Chesney and planned to “pass him a note” during the event. But before she could, the actor and singer’s publicists began talking and Zellweger’s intentions were communicated. “When the broadcast wrapped, [Chesney] went over [to Zellweger] and said, ‘I hear you are trying to pass me a note — don’t let the principal find out,'” a friend of Zellweger’s told People.
The pair did a surprisingly good job of keeping their relationship under wraps for months. It wasn’t until late April, when Zellweger came out on stage during Chesney’s concert to give him a margarita and a kiss that their relationship made its way into the public eye.
Just over a week later, the couple surprised the world once more when they wed in an intimate ceremony in the Virgin Islands.
Why We Loved Them: Though the relationship itself began and ended within a year, it seems Chesney had harbored something of a crush on Zellweger for quite some time. When asked to name the “three sexiest people” in 2002, he chose Zellweger (as well as Charlize Theron and Janet Jackson). “Here’s a country girl who’s still down to earth. You never see her coming, then—wham!—there she is. And that makes her really, really sexy,” he told The Tennessean. “Plus she seems like the kind of girl who could fit in and be at home anywhere.”
And in addition to being “sexy” and “down to earth,” Chesney also recognized Zellweger’s talent — he was so stirred by how she delivered her famous line in Jerry McGuire (“You had me at hello”) that it inspired him to write a song about it: “You Had Me from Hello.” “When Renée Zellweger said that line, I thought, ‘That could be a great song,’” he told People in 2000.
When They Peaked: For a (brief) time, Chesney and Zellweger were blushing newlyweds. The Cinderella Man star went on The Tonight Show with Jay Leno just two weeks after her wedding and gushed about her “cute” beau and meeting his “great” family — which included a man by the name of “Uncle Butch.”
The Breakup: Where do we even begin … Four months after the pair’s picturesque wedding, Zellweger filed to annul her marriage to Chesney, citing “fraud” as the driving factor. Once the public got a hold of the cryptic reason, people began to speculate that “fraud” was code for “Chesney is gay.” The outpour was so intense that Zellweger released a statement to “clarify that the term ‘fraud’ as listed in the documentation is simply legal language and not a reflection of Kenny’s character. I would personally be very grateful for your support in refraining from drawing derogatory, hurtful, sensationalized or untrue conclusions and greatly appreciate your understanding that we hope to experience this transition as privately as possible.”
Unintentionally complicating things further, the former couple released another statement clarifying that “the miscommunication of the objective of their marriage at the start is the only reason for this annulment. Renée and Kenny value and respect each other and are saddened that their different objectives prevent the success of this marriage.” Exactly what their respective marriage “objectives” were is unclear.
Despite Zellweger’s protestations, rumors continued to surface. The speculation clearly began to grate on Chesney. In 2009 he opened up to Playboy about the rumor, explaining, “That is the most unbelievable thing in the world … What guy who loves girls wouldn’t be angry about that sh—? I didn’t sign up for that. I think people need to live their lives the way they want to, but I’m pretty confident in the fact that I love girls. (laughs) I’ve got a long line of girls who could testify that I am not gay.” OK, Kenny. “In order for us to get an annulment, the legal papers could claim either physical abuse, which wasn’t true, or three or four other things that also weren’t true. The best thing we could put in there was fraud. So I said, ’All right, do it. Whatever,'” he said in regard to the notorious “fraud” citing.
In 2010, Chesney finally revealed why he and Zellweger split, telling Oprah Winfrey, “I panicked.”
“I look at my life as a box. … So everything that I put in — learn how to play guitar, put that in the box. The friends I made. I put that in the box, and my career grew. That box built grew into this wonderful house… And you protect everything and all the relationships and all the people that helped you build that house,” he told the talk show host. As for his marriage? Chesney admitted “It was out of the box,” explaining, “[Renée’s] a sweet soul, no doubt about it, but I just wasn’t ready…. This is the first time I’ve actually talked about it, but that’s what happened.”
More than a decade following her 225-day marriage, Zellweger opened up about the rumors that plagued Chesney, telling The Advocate, “It made me sad that somehow people were using that as a way to be cruel and calling someone gay as a pejorative, which has fateful consequences.”
Where They Are Now:
Zellweger split from longtime boyfriend Doyle Bramhall II earlier this year. At the time of her September Vulture profile, the actress said she was single.
She stars in her first major film in years with Judy Garland biopic Judy, and she’s already receiving Oscar buzz for her performance.
Chesney was most recently romantically linked to Mary Nolan.
The singer is currently gearing up for his 2020 Chillaxification Tour.