Stewart began his career in his hometown of New Orleans, Louisiana, at WDSU and WWL-TV, serving as an associate producer for the station's morning newscasts. During that time, Stewart also hosted the 10am - 3pm shift on then Top 40 formatted radio station KUMX, "Mix 104.1", (now KOBW).
His parents pushed him into show business at an early age. In 1993, he was a finalist on Star Search in the Teen Vocalist category.
In 2001, Stewart moved to WRBL in Columbus, Georgia to anchor that station's weekend newscasts. He was soon promoted to anchor of the 5 and 5:30pm weekday newscasts and served as that station's senior producer. Stewart won several awards for his reporting while at that station. During his time in Georgia, Stewart also hosted various music radio programs on WCGQ Q 107.3 and WRLD-FM Boomer 95.3, under the air name Kris Kennedy. Stewart left WRBL in 2006, moving to Norfolk and that city's CBS station WTKR.
Stewart is a former member of the NLGJA, a U.S. based organization of lesbian and gay journalists.
Stewart is a vocal supporter of local music artists. He also publicly supports Hope House[disambiguation needed], a Norfolk area non-profit agency which helps adults with developmental disabilities lead independent lives. He also participates in the annual Special Olympics Virginia's Polar Plunge.
Stewart was born in April 1977, in Marrero, Louisiana. He graduated from L.W. Higgins High School in 1994. He is divorced and currently lives in Norfolk, Virginia with his pet monkey, Bernard.