He is perhaps best known for his work on the critically acclaimed HBO series The Wire, where he directed six episodes and served as co-executive producer for three seasons.
[1] He has also produced and directed several other popular cable television programs, including CSI: Miami, Fringe and Chicago Fire.
Chappelle wrote and directed the political thriller An Acceptable Loss, starring Tika Sumpter and Jamie Lee Curtis, which was released by IFC Films in January 2019.
He went on to direct the horror sequel Halloween: The Curse of Michael Myers (1995) and shot additional scenes for Hellraiser: Bloodline (1996), replacing Kevin Yagher due to his fallout with the studio over creative differences.
In 2002, Chappelle became a director for three new series; the 2002 reimagining of The Twilight Zone, HBO crime drama The Wire and the procedural spin-off CSI: Miami.
[citation needed] Chappelle joined the crew of the HBO crime drama The Wire as a director for the first season in 2002.
[7][8] "Middle Ground" received the show's only Emmy Award nomination, for writers Simon and George Pelecanos in the category Outstanding Writing for a Drama Series.
Chappelle and the other senior producers were nominated for a BAFTA Award for Best International Series at the 2009 ceremony for their work on the fifth season.
He directed a further six episodes; "Dead Zone", "Hurricane Anthony", "Big Brother", "Slow Burn", "Not Landing" and the season finale "Innocent".
He directed a further six episodes for the season; the premiere "Resurrection", "Wrecking Crew", "Power Trip", "Smoke Gets in Your CSI's", "Flight Risk" and the finale "Seeing Red".
In winter 2012–2013, Chappelle joined the crew of the crime drama Chicago Fire as executive producer, and in five episodes as director.
In May 2017, Chappelle left Chicago Fire to begin production on his independent film An Acceptable Loss (formerly The Pages).
The film, a political thriller starring Tika Sumpter and Jamie Lee Curtis, marked Chappelle's return to feature filmmaking after over 15 years of working in television.