He made his acting debut in a Levi's commercial after being hired by his aunt who is a casting director, Amy Sobo.
[1] After enrolling in high-school drama classes, in 1993 he was cast in the NBC Saturday morning sitcom Running the Halls, which ran for one season.
He went on to guest star on My So-Called Life, Family Matters, The Parent 'Hood, The Fresh Prince of Bel-Air, Sister, Sister, The Burning Zone, The Steve Harvey Show, Beyond Belief: Fact or Fiction, Mercy Point, Nikki, JAG, It's All Relative and Courting Alex.
Kirkwood's most notable role to date was as Jerry "Rev" Harris in the 2000 Disney film Remember the Titans.
Kirkwood co-starred in Why Do Fools Fall in Love and the Disney Channel Original Movie Hounded with Tahj Mowry (Nominated for an Emmy Award for Best Supporting Actor - Comedy or Musical).