These artists include Joe, for whom Woodruff has directed 9 music videos since 1994, and Toni Braxton, with whom he has worked 10 times since 1996.
Woodruff directed the videos for some of Braxton's biggest singles, including "Un-Break My Heart", "You're Makin' Me High", and "He Wasn't Man Enough".
Rumors stated singer and actress Aaliyah was originally slated to play the title role, but died before filming began.
In 2015, Woodruff directed Honey 3 in South Africa with new fresh Talent including Bobby Lockwood and 'Kenny Wormald.
Since 2016, he has directed numerous episodes of the following television series: Hit the Floor, Star, Empire and Black Lightning.