The Legend of Bagger Vance (2000)

Will Smith stars as the titular caddy/guru in perhaps the ultimate expression of the "Magical Black Man" meme, The Legend of Bagger Vance (2000). Rannulph Junuh (Matt Damon) is having trouble re-adjusting to civilian life after returning home from serving in WWI. When he is recruited to participate in an exhibition golf game against two of the world's best players, Rannulph resigns himself to failure...until magic caddy Bagger Vance (Smith) teaches him the secrets of life, love, and the ultimate golf swing. Charlize Theron co-stars as Damon's love interest, and although she doesn't do a proper nude scene, if you pause at the 13-minute, 24-second mark, you can peep her pink pokies sticking out through her shirt. Bagger Vance won't leave you with baggy pants.