Shortly after the release of Hard Candy, tabloid headlines made note of Madonnas budding friendship with Yankees star Alex Rodriguez. While everyone speculates about the status of Madonnas marriage to director Guy Ritchie, this much is known: Madonna has previously shown an affinity for sports. The artist was paired with NBA star Dennis Rodman in the mid-90s. (Jacques Brinon / Associated Press Jacob Andrzejczak / Getty Images)
Tennis pro Andy Roddick has had trouble besting Roger Federer, but Roddick has probably spent more time in the tabloids. In the mid-2000s, he dated singer/actress Mandy Moore. The two have since split. (Genaro Molina / Los Angeles Times Carl de Souza AFP/Getty Images)
Sheryl Crow and Lance Armstrong
The Grammy-adored singer began dating the world champion cyclist in 2003. The couple was engaged but never married. Gossip hounds can look to Crows recent album Detours and the adult relationship themes of songs such as Diamond Ring to gain some insight. Or not. (Jo Hale / Getty Images Michael Dwyer / Associated Press)
Victoria and David Beckham
The soccer star and the Spice Girl reportedly met at a charity event in 1997, and the couple has been a tabloid fixture since. The two made massive headlines when they moved to Los Angeles in the summer of 2007. (Wally Skalij / Los Angeles Times)
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Pink and Carey Hart
Pop star Pink once sang that not even an 18-wheeler could keep her down, but a man driving a two-wheeler could certainly win her heart. Pink dated motocross racer Carey Hart in the mid-2000s, later marrying the extreme sports star. The two split in early 2008. (Anne Cusack / Los Angeles Times John Bramley / Touchstone)
Alyssa Milano and Brad Penny
Before Milano, who had a handful of hit pop albums in Japan, was designing a line of baseball-inspired fashions, dubbed Touch, she was getting an intimate look at the sport courtesy of boyfriend Brad Penny. The pair have since split up, but Milano has been associated in the tabloids with a host of baseball stars, including pitcher Carl Pavano and catcher Russell Martin.
(OK, so perhaps it’s a stretch counting Milano as a pop singer here, but we needed 10 slides. And here’s proof.) (Noah Berger / Associated Press Carlos Chavez / Los Angeles Times)
Carrie Underwood and Tony Romo
Dont have to worry about Underwoods smash Before He Cheats being inspired by Romo. The pair were close, but not close for long. While the two went to some high-profile events together, Underwood said to EW.com last year, I don’t know if it’s that I’m not quite his type or whatever, but I don’t think he’s at the point in his life where he would be willing to sacrifice football. (Gina Ferazzi / Los Angeles Times Tim Sharp / Associated Press)
Jessica Simpson and Tono Romo
Perhaps the Dallas Cowboy QB just wasnt a big fan of country. Romo began dating pop star Jessica Simpson in late 2007. While the tabloids seem pleased, fans have targeted Romos Hollywood relationships every time he has a bad performance. (Tony Gutierrez / Associated Press)
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Heather Headley and Brian Musso
The pop-R&B singer and Broadway star (The Lion King) reportedly dropped out of school for a role in Ragtime, but Northwestern is still a part of her life in a way. Headley married fellow Wildcat and former New York Jet Brian Musso. (Joan Marcus Jonathan Daniel / Allsport)