The Odd Couples

Ashton Kutcher and Rihanna, Jennifer Lopez and Casper Smart, & More Odd Celebrity Rebounds (PHOTOS)

While Battleship star Rihanna  denies any rumors that she’s dating Two and a Half Men’s Ashton Kutcher, we can’t help but wonder why she was seen leaving his house this week at four in the morning. Freshly separated from wife Demi Moore, Kutcher doesn’t seem like he’ll be settling down any time soon. But what about RiRi? Having recently been linked to once-abusive ex-boyfriend Chris Brown, the “We Found Love” singer was quick to deny rumors she was seeing Kutcher. But if the late-night visit does indeed turn into something more permanent, it seems like an odd coupling. We take a look at some of the strangest celebrity rebounds.

AP Photos (3); Getty Images (top right)

AP Photos (3); Getty Images (top right)

From Ashton Kutcher and Rihanna to ScarJo and Sean Penn, Hollywood’s most bizarre rebound relationships.

AP Photo (2)

Ashton Kutcher & Rihanna

While Battleship star Rihanna  denies any rumors that she’s dating Two and a Half Men’s Ashton Kutcher, we can’t help but wonder why she was seen leaving his house this week at four in the morning. Freshly separated from wife Demi Moore, Kutcher doesn’t seem like he’ll be settling down any time soon. But what about RiRi? Having recently been linked to once-abusive ex-boyfriend Chris Brown, the “We Found Love” singer was quick to deny rumors she was seeing Kutcher. But if the late-night visit does indeed turn into something more permanent, it seems like an odd coupling. We take a look at some of the strangest celebrity rebounds.

Gustavo Caballero / Getty Images

Madonna & Jesus Luz

After her eight-year marriage to Guy Ritchie fizzled out in October 2008, Madonna was seen canoodling with Brazilian model Jesus Luz only two months later. Fifty-three year-old Madonna was 28 years his senior during their fling. These days, she’s dating 24-year-old French dancer Brahim Zaibat, continuing her cougar-esque tendencies.

Kevin Mazur, WireImage / Getty Images

Jennifer Lopez & Casper Smart

Jennifer Lopez and Marc Anthony spent seven years as a married couple, and just four months after their separation, Lopez stepped out in public with her backup dancer, 24-year-old Casper Smart. The 42-year-old American Idol judge has been dating Smart for more than five months, and we hope their relationship lasts longer than the likes of Britney Spears and Kevin Federline, another songstress who turned her backup dancer into a leading man.

Matt Sayles / AP Photo

Mel Gibson and Oksana Grigorieva

Braveheart actor Mel Gibson was photographed with Russian singer-songwriter Oksana Grigorieva just one month before his wife Robin—mother to his seven children—filed for divorce after 28 years of marriage.  Gibson and Grigorieva met on the set of The Edge of Darkness, and after a year of dating, a child, and a very public airing of a recorded conversation the pair had in which Gibson proved he was both violent and misogynistic, the couple called it quits.

Gene Young, Splash News / Newscom

Scarlett Johansson & Sean Penn

Three months after her separation from Hollywood heartthrob Ryan Reynolds, Scarlett Johansson fell into the arms of two-time Academy Award winner Sean Penn (24 years her senior). The couple didn’t avoid the limelight, taking off for Mexico for a week and showing up to Reese Witherspoon’s wedding together.

Lester Cohen, WireImage / Getty Images

Jennifer Love Hewitt & Jamie Kennedy

After a 14-month engagement to Scottish actor Ross McCall, Love Hewitt called it quits and began dating her Ghost Whisperer co-star Jamie Kennedy. While the two were only together a year, Kennedy was enthusiastic about their relationship, comparing it to the famed romance in the Twilight series. “We’re more than dating, we’re more than in love,” he told Ryan Seacrest in a radio interview. “We have an intense connection. She’s my Bella. I don’t want to bite her neck, but I want her to live.”

Getty Images (2)

Eddie Murphy & Melanie Brown

In a jaw-dropping pairing, Spice Girl Melanie Brown (Scary Spice) hooked up with Eddie Murphy in the summer of 2006, just months after the funnyman divorced Nicole Mitchell, his wife of 12 years. When Brown learned she was expecting a child, Murphy said of the pregnancy, “We’re not together anymore, and I don’t know whose child that is, until it comes out and has a blood test. You shouldn’t jump to conclusions.” But Brown only learned that her relationship with Murphy was over after receiving voicemails from friends informing her of the interview.

Peter Kramer / AP Photo

Justin Timberlake & Cameron Diaz

Britney Spears and Justin Timberlake were America’s dream couple. Both blond, pop-singing former Mickey Mouse Club members, the couple dated for three years until unexpectedly calling it quits. A music video for Timberlake’s “Cry Me a River” that featured a Spears look-alike fueled rumors she had cheated on him. But in 2003, Justin hooked up with Charlie’s Angels actress Cameron Diaz, and the pair dated for more than three years until breaking it off in 2007. Timberlake is now engaged to 7th Heaven hottie Jessica Biel.

Sipa

Renee Zellweger & Kenny Chesney

Bridget Jones’s Diary star Renee Zellweger split from White Stripes rocker Jack White in December 2004—but just five months later was hitched to country crooner Kenny Chesney. This rebound may have happened a little too fast, as they had their marriage annulled four months after their idyllic St. John wedding, with the actress citing “fraud” as the reason. 

Ric Francis / AP Photo

Tom Cruise & Penelope Cruz

Mission Impossible’s biggest asset, Tom Cruise, filed for divorce in 2001 after 10 years of marriage to wife Nicole Kidman. Before his eventual marriage to Katie Holmes, Cruise had a short, on-and-off fling with Vanilla Sky co-star Penelope Cruz. The Cru(i)z(es)’s relationship ended as the pair cited "irreconcilable spelling differences.”

Peter Kramer / Getty Images

Richie Sambora & Denise Richards

Denise Richards split from hubby Charlie Sheen in 2006, and Bon Jovi guitarist Richie Sambora parted ways with wife Heather Locklear the same year. Unfortunately, Richards and Locklear were still best friends when Richards started seeing Sambora in 2006. The newly divorced stars dated for about a year before calling it quits. But in 2011 the pair got back together, and Richards even wrote about Sambora in her memoir, The Real Girl Next Door, saying, “Richie and I shared an easiness I hadn't before had. We were able to be open, honest, and completely authentic with each other, with no judgment."

Derek Storm, Everett Collection / Newscom

Susan Sarandon & Jonathan Bricklin

After 23 years as a couple, Susan Sarandon separated from partner Tim Robbins and set her sights on something new. Falling into the lap of 31-year-old ping-pong guru and business partner Jonathan Bricklin, Sarandon is 32 years his senior. According to a recent report, Sarandon is finally out of the closet with their relationship, confirming the two-year relationship. “You can say… we are collaborating in a lot of different areas,” she told People magazine.

Evan Agostini / AP Photo

Kim Kardashian & Kris Humphries

After many years of off and on dating, Kim Kardashian called it off with the Miami Dolphins’ Reggie Bush. It didn’t take her long to fall into the arms of the New Jersey Nets’ Kris Humphries. The pair dated for several months before tying the knot in an over-the-top, televised wedding. As if you didn’t already know, the pair split after just 72 days as man and wife, and the rest is history.