In Cedar Rapids, Iowa, Larry and Diane Kutcher welcome the birth of twin boys. Christopher Ashton Kutcher follows five minutes after his fraternal brother Michael, who was born with a mild form of cerebral palsy.
In the middle of his parents' divorce, Kutcher's twin brother Michael, 13, receives a life-saving emergency heart transplant after suffering from a viral heart inflammation and going into cardiac arrest. "Ashton never left my side," Michael, now healthy, later tells PEOPLE. "He showed me the love one brother has for another." Two years later, Kutcher's mom relocates the family – the twin brothers and older sister Tausha – to Homestead, Iowa, where they eventually move into a new house with stepfather Mark Portwood.
While studying biochemical engineering at University of Iowa and working in a General Mills factory sweeping Cheerios dust, Kutcher enters the Fresh Faces of Iowa modeling contest and wins a trip to New York City to pursue a contract with model agencies.
After three days in New York City, Kutcher signs a modeling contract with the Next agency. Soon, the handsome Iowa boy is walking down fashion runways from Paris to Milan and popping up in Calvin Klein jean ads.
While modeling for Abercrombie & Fitch clothing, Kutcher meets fellow model January Jones. After dating for three years, Kutcher and Jones call it quits in 2001.
Kutcher lands the role of the handsome but airheaded Kelso on the Fox series That '70s Show. The show, a satirical throwback to comedies of the 1970s, requires Kutcher's character to wear bellbottoms and vintage shirts while sporting a long feathered haircut.
With his TV fame growing, Kutcher tries his hand at movies with a small role in Coming Soon, starring Gaby Hoffmann and Mia Farrow. He continues his film career with two more small roles in Down to You and the box office flop Reindeer Games the following year.
His model good looks earn Kutcher a spot on PEOPLE's annual 50 Most Beautiful People In the World list. "He's got very nice lips," '70s costar Mila Kunis tells PEOPLE. "He's also got nice deep eyes, nice bone structure and a toned body. He's a hottie." Kutcher will reappear on the list in 2003.
Kutcher plays to his '70s Show type in Dude, Where's My Car? with Seann Williams Scott, as two potheads who retrace their steps after a crazy blackout night. Panned by critics, the slacker comedy earns $41 million its first month at the box office.
Kutcher starts a nine-month relationship with actress Ashley Scott from the TV series Dark Angel. Of their parting, Scott later tells PEOPLE they were both "going in different directions."
BIOGRAPHY (top to bottom): SPLASH NEWS; DIANE PORTWOOD; PACIFIC COAST NEWS; Jeff Vespa/WIREIMAGE; CARIN A. BAER/FOX; 20th Century FOX/Everett; Peter Brooker/REX USA