Throughout his Hollywood career, Montgomery Gentry had a variety of powerful musical performances. Gentry worked on a variety of projects during his early entertainment career, including "35th Annual Academy of Country Music Awards" (CBS, 1999-2000), "CMT All Access: Joe Diffie" (CMT, 1998-99) and "NASCAR Rocks I" (The Nashville Network, 1998-99). He also contributed to "TNN Music City News Country Awards" (The Nashville Network, 1998-99), "The 27th Annual American Music Awards" (ABC, 1999-2000) and "The 34th Annual Academy of Country Music Awards" (CBS, 1998-99). In the early 2000s, Gentry devoted his time to various credits, such as "The 34th Annual CMA Awards" (CBS, 2000-01), "CMT Crossroads" (CMT, 2001-) and "The 36th Annual Academy of Country Music Awards" (CBS, 2001-02). He also worked on "The Country Freedom Concert" (CMT, 2001-02). Additionally, he could be seen on a variety of television specials like "Boyz in the Woodz" (2004-05), "CMA Music Festival: Country Music's Biggest Party" (ABC, 2004-05) and "I Walk the Line: A Night for Johnny Cash" (CBS, 2005-06). Gentry also contributed music to the Larry the Cable Guy comedy "Larry the Cable Guy: Health Inspector" (2006). Gentry most recently appeared on "The 44th Annual Academy of Country Music Awards" (CBS, 2008-09).