He is best known for his television roles as the bass singer Melvin Franklin in The Temptations, Robin Wood in Buffy the Vampire Slayer, Malcolm Franks in Single Ladies, and Jeff Malone in Suits, Dr. Joseph Prestridge in Parenthood, the angel Amenadiel in Lucifer, and Wayne Palmer in the thriller series 24.

Woodside made a guest appearance on JAG in its final season as FBI agent Rod Benton.

From 2002 to 2003, he starred in 14 episodes of the final season of Buffy the Vampire Slayer as Robin Wood, the Principal of Sunnydale High School.

In 2007, he was a guest star on Grey's Anatomy in the show's 4th-season episode "Forever Young" wherein he played the character of Marcus.

From 2011 to 2014, Woodside starred as Malcolm Franks on the VH1 series Single Ladies, playing opposite LisaRaye McCoy as Keisha Greene.