Woodbine was born on April 13, 1973 in Harlem, New York. He attended the Dalton School on Manhattan’s Upper East Side, before transferring to the Fiorello H. LaGuardia High School of Music & Art and Performing Arts in the city.

In 1996 he appeared in Shakur’s music video for “I Ain’t Mad at Cha” and formed a friendship with the rapper. They subsequently reunited in Vondie Curtis-Hall’s directorial debut, Gridlock’d, which was released four months after Shakur’s death.

In 2009, Woodbine appeared in the blaxploitation film Black Dynamite and followed it up the next year with the M. Night Shyamalan-produced supernatural thriller Devil. He has also appeared as a police officer on the critically acclaimed series Southland (2011). He next appeared in the 2012 remake of Total Recall and then Riddick the next year.

In December 2015, he received a Critics’ Choice Television Award nomination for Best Supporting Actor in a Movie/Miniseries for his role as Mike Milligan in Fargo.

In 2017, Woodbine appeared in the Sony Pictures and Marvel Studios film Spider-Man: Homecoming, as Shocker, one of four villains, alongside Michael Keaton, Logan Marshall-Green and Michael Chernus.

In 2018, Woodbine starred in the series Unsolved. He played Daryn Dupree, who was part of a police task force that investigated the murders of rappers Notorious BIG and Tupac Shakur.