3. 'Dazed and Confused' (1993)
Inspired by McConaughey's adoring childhood vision of his chick-magnet older brother — "He was the coolest cat going, man," the actor once said — David Wooderson is our modern Peter Pan, all dopey smile and endless freedom. No such guy probably exists in real life, but that's the point: Plenty of men see in Wooderson an idealized version of no-strings-attached grownup swagger that they know they'll never attain. McConaughey's first onscreen role was so instantly iconic, so tossed-off natural, that it risked pigeonholing him. Years later, though, his Dazed and Confused breakthrough now stands as a guiding light for everything that's come after: effortlessly charming, deeply lovable, no big deal yet one-of-a-kind.