Jesse Bradford

After his breakout role in the 1990 film Presumed Innocent, Jesse Bradford appeared in films like King of the Hill, Hackers and director Baz Luhrmann’s Romeo + Juliet before landing his role in Bring It On.

In the film, he played Missy’s cheeky brother Cliff, who Dunst’s Torrance inevitably develops a crush on. While the film remains one of his most notable roles, the 41-year-old went on to star in Swimfan opposite Erika Christensen and Clockstoppers in 2002. He later appeared in Clint Eastwood’s critically acclaimed Flags of Our Fathers in 2006. Over the years, Bradford has also appeared in TV’s The West Wing, Outlaw, NCIS and more recently Shooter. In 2018, he tied the knot with Brazilian actress Andréa Leal.