The future University of Texas frat boy is voted Most Handsome at Longview (Texas) High School. According to his mom, the popular golf and tennis player has no shortage of female admirers. "I'm telling you, those girls liked his butt," she tells PEOPLE.
Along with a cast of future stars, including Ben Affleck and Milla Jovovich, McConaughey makes a memorable film debut as stoner icon David Wooderson in the high school flick Dazed and Confused. He later names his production company Just Keep Livin', a line his character improvises in the movie.
McConaughey terrorizes Renée Zellweger (left) in The Return of the Texas Chainsaw Massacre, a limited-theater release that becomes a kitschy collector's item after both find stardom. Despite the film's obscurity, the Dallas Observer writes, "McConaughey's Nicholson-level deranged performance as the lead bad guy – a rompin', stompin', hootin', hollerin', homicidal, cannibal cowpoke – makes it truly special."
Based on his casting in the upcoming film A Time to Kill, McConaughey shares the cover of Vanity Fair's annual Hollywood issue with fellow up-and-comers Leonardo DiCaprio and Tim Roth. Four months later, he again makes the cover, this time solo.
With his role as Southern lawyer Jake Brigance in the adaptation of John Grisham's A Time to Kill, McConaughey establishes himself as a bona fide rising star. He proves to be an adept leading man offscreen as well, briefly romancing costar Ashley Judd during filming and striking up a close friendship with fellow lead Sandra Bullock as well.
"He's become a powerful force in my life," Bullock tells London's Express on Sunday about her relationship with McConaughey. "We have fabulous chemistry together." Despite being seen frequently in public for more than three months, including a New Year's Eve celebration at Commander's Palace in New Orleans and several joint vacations, McConaughey and fellow Texan Bullock refuse to acknowledge a romantic connection. Friends and publicists continue to insist they are just friends. Regardless of the nature of their relationship, the pair will stay close over the years.
The premiere of Robert Zemeckis's outer-space epic Contact, also starring Jodie Foster (left), marks the first of two films McConaughey makes with a high-profile director this year. In December, he stars as a mid-19th-century lawyer in Steven Spielberg's slave drama Amistad.
As a video store clerk turned 24-hour reality show subject in Edtv, McConaughey appears in his first leading comedy role. While most critics agree that McConaughey shines as the star, the Ron Howard film is a commercial disappointment, earning $22 million in the U.S.
Responding to a noise complaint, police arrest McConaughey on suspicion of marijuana possession and resisting arrest in Austin, Texas. Police say they arrived at his house and found the actor dancing naked while playing the bongos. After spending nine hours in jail, McConaughey says, "I don't want to rent a place there, but it was a nice stay for a night." He pays a $50 fine and is released.
With his good looks and down-home charm, it makes sense for McConaughey to take on romantic comedies. He stars alongside Jennifer Lopez as the handsome doctor she falls for in The Wedding Planner. He continues breaking hearts in 2003's How to Lose a Guy in 10 Days opposite Kate Hudson and 2006's Failure to Launch with Sarah Jessica Parker. He's often seen flaunting his fab abs both on and off the screen.
BIOGRAPHY (top to bottom): Classmates Yearbook Archives; Everett/REX USA; Everett Collection; Warner Bros.; Janet Gough/Celebrity Photo; Everett Collection; Kobal Collection/Wireimage; AP; Ginsburg/Spaly/Splash news