Ashton Kutcher's 10 Hottest Hook-Ups

Image via Complex Original

Ashton Kutcher is known to make his rounds in Hollywood. The 34-year-old Two and a Half Men star has had the pick of the litter since bursting onto the scene in 1998 as Kelso on That '70s Show. Although he's been in a few long-term relationships, most notably a six-year marriage to Demi Moore, no one has been able to tame the kid from Iowa, who seems to thrive on the the thrill of the chase.

From actresses to pop stars and mistresses, he's conquered them all. Check out this list of Ashton Kutcher's 10 Hottest Hook-Ups and you'll see exactly why the trucker hat-wearing bachelor loves the single life.

TARA REID

When: 2003 

Ashton and Tara starred in My Boss's Daughter together. The very next year, Reid was a subject of one of Kutcher's many celebrity pranks on Season 3 of Punk'd. The two were friends and definitely partied together on more than one occasion. Tara wasn't exactly an innocent starlet back then, as she had previously been linked to the likes of Carson Daly and Fred Durst. So, Ashton knew exactly what he was getting himself into when he signed on to star opposite Tara.

Smash Probability: Ashton was in cahoots with Demi Moore before My Boss's Daughter hit the box office, but seeing as how Tara Reid was widely regarded as Hollywood's hottest harlot, we wouldn't put it past Ashton to toot it and boot it.

ASHLEY SCOTT

When: 2001-2002

Shortly after splitting with January Jones, Ashton jumped into a nine-month relationship with Dark Angel actress Ashley Scott. Although she had a lucrative TV gig, Ashton seemed to have loftier goals and was looking to make a high-profile upgrade to a big-screen starlet. In the end, Ashton and Ashley were in different places in their respective careers. Ashton had both successful TV and movie ventures and Punk'd was on the horizon, while Scott's career prospects weren't nearly as promising. The writing was on the wall.

Smash Probability: At the time, the world was Ashton's oyster and he took what he wanted.

DEMI MOORE

When: May 2003-November 2011

When Demi and Ashton first got together, many news outlets were quick to point out the couple's gap in age, Demi being 15 years Ashton's senior. Nonetheless, the pair got married two years after they met. The rumor was that they had an open marriage and that Ashton and Demi could satiate their sexual appetite outside of the marriage. The 49-year-old actress filed for divorce from the Two And A Half Men star in November 2011, stating, "As a woman, a mother and a wife, there are certain vales and vows that I hold sacred, and it is in this spirit that I have chosen to move forward with my life." If by moving forward she meant doing whippets and subsequently checking into rehab, then she has carried on just fine.

Smash Probability: They were married for over six years. C'mon son!

BRITTNEY JONES

When: July 2010

In this instance, it's not so much about the girl involved as it was about the details of how it all went down. Accordingly to Star, the two allegedly met while bowling in an adjacent lanes at Hollywood's Lucky Strike. Ashton was with Demi and Rumor at the time, but that didn't stop him from discretely sliding Jones his number on a napkin. They began exchanging texts shortly thereafter. It wasn't Ashton pushing the action, however. Rather, it was Jones who sent the suggestive texts and coordinated the trysts.  

Smash Probability: They allegedly met up at the Kutcher residence for sex when Demi was out of town, but the actor had a strict couch-only policy, as he did not want to soil the expensive linens.

JANUARY JONES

When: 1998-2001

January Jones scooped up Ashton Kutcher right as he began his 8-year run on That '70s Show. They stayed together for three years, during which Kutcher starred in the cult classic stoner comedy Dude, Where's My Car? Their romance fizzled out soon after, though. According to the Mad Men actress, Kutcher wasn't a good boyfriend. "He was not supportive of my acting," Jones told GQ in 2009. "He was like, 'I don't think you're going to be good at this.' So, fuck you!" What a difference a decade makes.

Smash Probability: Three years in Hollywood is a long time, especially when your rise to celebrity status happens seemingly overnight like it did for Ashton in 1998.

BRITTANY MURPHY

When: 2002-2003

They started dating in late 2002 after filming Just Married. However, their fling ended abruptly after seven months, to the surprise of Ashton and Brittany's friends and family. "He likes going out all of the time, and she's more of a homebody," a source close to the situation later explained. Nevertheless, the two remained friends up until the actress' untimely death in December 2009. Upon hearing the news of Murphy's passing, @aplusk took to Twitter: "2day the world lost a little piece of sunshine. My deepest condolences go out 2 Brittany’s family, her husband, & her amazing mother Sharon." He concluded with, "see you on the other side kid." 

Smash Probability: During an MTV interview to promote Just Married, Murphy revealed the key to a lasting romance, saying, "I mean, to have a healthy sexual relationship with your partner, I think that's important." We are willing to bet she practiced what she preached with her co-star.

NELLY FURTADO

When: Unknown

The two supposedly hooked up before Ashton gained notoriety on That '70s Show. In 2006, the singer revealed on Australian pop radio that she dated Kutcher way back when. "Before he was really big," she gushed. "Yeah, we kissed like once or twice. It was good."

Smash Probability: Kissing often leads to other things, but Furtado's coy response doesn't lead us to believe she was anything close to a promiscuous girl when the two dated.

AMY SMART

When: 2003

Moving from one co-star to the next, Ashton Kutch met Amy Smart while filming The Butterfly Effect. Smart caught notoriety for her role in Road Trip, and her career was just starting to pick up steam. Although she was object of Kutcher's affection, there was one small detail that prohibited the would-be from playing kiss and tell: Smart was already in a longterm relationship with actor Branden Williams. Nonetheless, speculation of a possible hookup persisted through the movie's January 2004 release, but died down soon thereafter. 

Smash Probability: Co-stars fraternizing while filming a movie is a time-honored Hollywood tradition. Smart had a boyfriend at the time, so anything that may have taken place was effectively kept under wraps.

MILA KUNIS

When: April 2012

Ashton allegedly rebounded withThat '70s Show co-star Mila Kunis after his very public divorce from Demi Moore. The two had been friends since their sitcom days, but rumors of a romantic relationship began to swirl when they were spotted out together on what appeared to be a date in L.A. Days later, a rep for Mila denounced the new couple rumors. "They are not dating," stated the rep. "They’ve been friends for years and they had dinner with a bunch of friends." 

Smash Probability: Kutcher starred in No Strings Attached. Kunis starred in Friends With Benefits. Sometimes art can, in fact, imitate life.

RIHANNA

When: March 2012

In March 2012, Rihanna was reportedly partying with friends at Colony nightclub in L.A. when she got a text message from Ashton Kutcher around midnight. The singer promptly exited the club and paid a visit to the Kutcher's house, where she stayed until 4 in the morning. Immediately following the late night rendezvous there was plenty of speculation about the nature of their relationship. Rihanna shot down rumors that the two were secretly dating and even ethered a British reporter for asking about it. 

Smash Probability: Their reputations precede them. That's all we can say.