His ninth chart entry came in late 2008-early 2009 as a guest vocalist on Kenny Chesney's cover of his 1990 single "Down the Road".

In addition to his work as a solo artist, McAnally has written number-one singles for Alabama and Shenandoah, as well as songs for Sawyer Brown and T.G.

He also holds a number of credits as a session musician, and has produced for Sawyer Brown, Restless Heart, and Jimmy Buffett.

[2] Reviewing it in Christgau's Record Guide: Rock Albums of the Seventies (1981), Robert Christgau said, "although it does often sound pat, as folk stoicism will in a post-folk context, the first side comes across pretty outspoken for a Mississippi singer-songwriter with royalties in the bank—the heroine of one song is a rape victim who murders both assailant and judge after the latter lets off the former.

However, he found success as a songwriter for Jimmy Buffett, in addition to co-writing Alabama's Number One hit "Old Flame".

Mac eventually signed with Geffen Records with two albums (Nothin' but the Truth, which included the single "Minimum Love" which reached No.

Also that year, he produced Sawyer Brown's album The Dirt Road, and continued to produce almost all of their subsequent albums, in addition to co-writing several of the band's singles between then and the late 1990s, including the Number One "Thank God for You", as well as the Top Five hits "All These Years", "Cafe on the Corner", "The Boys and Me", and "This Time".

Throughout the 1990s, McAnally also found work as a session musician, playing guitar on several artists' albums, in addition to joining Buffett's road band.

One month later, McAnally signed to Show Dog Nashville, a label owned by Toby Keith.

In 2024, McAnally provided the voice of Terrence "Shaker" in the Country Bear Musical Jamboree at Walt Disney World's Magic Kingdom.