He has guest starred in The Wire as manipulative drug kingpin Proposition Joe on all five seasons of the show. The role has drawn acclaim for Chew both for his ability to handle the character's verbose, Dickensian dialogue and the sympathy he draws while playing a "bad guy".
Chew recalls that when he auditioned the other actors were all well groomed, well dressed and thinner than him. He later learned that the real-life inspiration for the characters was a charming and debonair drug dealer so he was surprised to have received the role. He was initially unsure as to how long the character would remain in the series and has been pleased to continue working on the show.
Chew also appeared on HBO's The Corner (created by David Simon like The Wire) and NBC's Homicide: Life on the Street (based on a book by Simon). He received all three roles through the Pat Moran casting agency. Simon has described Chew as a "smart, elegant actor" and stated that he has one of the most authentic Baltimore accents on the show.
Chew has also worked with children's theatre companies throughout his career including Playworks USA and later the Arena Players. Through his association with the Arena Players, Moran began to turn to Chew for help in casting local young actors for the show. He has provided more than twenty actors and more than six have had recurring roles including Melvin Russell (who plays Jamal) and brother and sister Rashad Orange (who plays Sherrod) and Rakiya Orange who plays Charlene Young.
Chew also worked as an acting coach with several of the young actors joining the show in the fourth season and with non-professional actor Felicia "Snoop" Pearson. As acting coach Chew was responsible for preparing the core of four new young actors Tristan Wilds, Julito McCullum, Maestro Harrell and Jermaine Crawford for their major roles in the fourth season. Chew describes his aim as helping the young actors find the roles within themselves and looking for what is real. Chew worked with Wilds to perfect the internalised build-up of emotion in his character, Michael Lee, and to convey the character through looks and physical acting rather than dialogue. Chew has remarked that he was also impressed with Wilds professionalism and commitment, McCullum's natural ability as Namond Brice, Harrell's charm as Randy Wagstaff and Crawford's honesty of performance as Duquan "Dukie" Weems. Chew finds working with young people rewarding because it allows him to see them develop and bring them to their full potential.
Chew also appeared in HBO films' Something the Lord Made. Chew appeared on Homicide, in the three part episode "Blood Ties", playing Wilkie Collins, a drug kingpin who hates violence; he provides the police with key information about what drug dealer was shooting at them so that they will not interfere with his business. He and his wife are subsequently murdered for his betrayal; his young son witnesses, and helps the police arrest Wilkie's murderer.