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.