Woodruff directed the 2003 film Honey. Singer and Actress Aaliyah was originally slated to play the title role, but died before filming began. She was replaced by Jessica Alba. The film was released on December 5, 2003 and opened at #2 at the US Box Office, earning $12,856,040 in its opening weekend. The film received generally negative reviews from critics, with a rating of 20% on Rotten Tomatoes, but favorable reviews from moviegoers, with a rating of 76% on Rotten Tomatoes.

Woodruff then directed the 2005 film Beauty Shop, a spin-off of the Barbershop film trilogy, starring Queen Latifah. The film was released on March 30, 2005 and went on to gross worldwide $37,245,453 at the worldwide box office. Movie critics' reviews were generally negative, generating a rating of 38% on Rotten Tomatoes. However, moviegoers liked the movie, giving it a 70% rating on Rotten Tomatoes.

He then directed the 2009 film Bring It On: Fight to the Finish, starring Christina Milian. The film was released straight-to-DVD on September 1, 2009.

He directed the straight-to-DVD sequel to Honey, Honey 2, which was released in 2011.

He released the movie Rags on Nickelodeon in 2012. He directed 7 episodes of The Game TV series in 2012 and 2013. Woodruff is currently directing Honey 3 in South Africa with new fresh Talent including Bobby Lockwood and Kenny Wormald. Woodruff directed the film adaptation of the best-selling novel of the same name Addicted (2014 film) and A Very Larry Christmas.