Ol' Dirty Bastard's career in Wu-Tang was marked by wild and criminal behavior. At the 1998 Grammy Awards, he protested the Clan's loss (in Best Rap Album) by interrupting Shawn Colvin's acceptance speech for her Song of the Year award. ODB was also arrested several times for a variety of offenses, including assault, shoplifting, wearing body armor after being convicted of a felony, and possession of cocaine.^[19] He was also in trouble for missing multiple court dates. In late 2000, Ol' Dirty Bastard unexpectedly escaped near the end of his rehab sentence, spending one month on the run as a fugitive before showing up on stage at the record release party for The W in New York City. Ol' Dirty Bastard managed to escape the club but was later captured by police in a McDonald's parking lot in Philadelphia and sent to New York to face charges of cocaine possession. In April 2001, he was sentenced to two to four years in prison.^[20] Once released from prison, he signed a one million dollar contract with Roc-a-Fella Records.

On November 13, 2004 – A date he was scheduled to perform with the rest of the Wu-Tang Clan at a reunion concert at Continental Airlines Arena, ODB collapsed at Wu-Tang's recording studio, 36 Chambers on West 34th Street in New York City.^[21] He was pronounced dead later that night, just two days shy of his 36th birthday. His funeral service was held at Brooklyn's Christian Cultural Center.

Wu-Tang has paid him homage on more than one occasion. In August 2006, one of his sons came out at a Wu-Tang concert at Webster Hall and rapped "Brooklyn Zoo", along with his mother. Also during a concert at the Hammerstein Ballroom the Clan brought his mother out on stage while the entire occupancy sang along to 

"Shimmy Shimmy Ya".