Kutcher, his brother, and their older sister Tausha stayed with their mother after the split. When their mother remarried, they moved to Homestead, a small farm community. In his new hometown, he continued to pursue his interest in acting, appearing in school productions. After his high school days drew to a close, Kutcher's rebellious side emerged. He was arrested for breaking into his school in his senior year and spent a lot of his time partying.
After graduating in 1996, Kutcher went to the University of Iowa to study biochemical engineering. He joined a fraternity and continued his partying ways for the first few months before hitting the books. In addition to his studies, Kutcher held a number of odd jobs to pay for school, including sweeping up cereal dust at a General Mills factory.
Before being approached a talent scout, Kutcher knew nothing of the world of male modeling. But that soon changed once he entered and won the Fresh Faces of Iowa modeling contest in 1997. This took him to New York City where he signed with a modeling agency. Some of his most famous gigs as a model were for designer Calvin Klein and for the Abercrombie & Fitch catalog. During the Abercrombie & Fitch shoot, Kutcher met future girlfriend, January Jones, a model and actress.
In the spring of 1998, Kutcher landed his breakthrough role on the popular retro sitcom, That '70s Show. The comedy followed the life of Eric Foreman (Topher Grace) and his teenage friends as they grew up in the small town of Point Place, Wisconsin. Appearing as the adorable, but dense Michael Kelso, Kutcher won over fans his broad humor and good looks. Mila Kunis played his on-again, off-again girlfriend Jackie, and Danny Masterson, Laura Prepon, and Wilmer Valderrama rounded out the rest of the cast as Steve Hyde, Donna Pinciotti, and Fez respectively. The young actors on the show developed a strong bond and were often seen out together in Los Angeles.
In addition to his work on the series, Kutcher started landing film roles. He had small parts in the private school comedy, Coming Soon (1999), the romantic comedy, Down to You (2000), with Freddie Prinze Jr. and Julia Stiles, and the crime drama, Reindeer Games (2000), with Ben Affleck. For his first leading role, Kutcher did not vary much from his television image. He played a wacky stoner who, along with his friend Sean William Scott, tries to retrace the previous night's events in Dude, Where's My Car? (2000). While it was derided by critics, the comedy was a box office hit. Kutcher developed quite a fan base and was named one of People magazine's 50 Most Beautiful People in the World that year.