Jimmy Fortune toured, sang and performed with the legendary Statler Brothers for 21 years. He joined them first as a temporary replacement for Lew DeWitt, after DeWitt heard him singing at a ski resort and recommended him. Following an audition in Nashville, Jimmy was contacted by the Statler Brothers and performed his first show with them on January 28, 1982, in Savannah, Georgia. Due to the debilitating effects of Crohn's Disease, Lew was unable to return to the stage with the Statlers, and Jimmy was hired as a permanent replacement in August of 1982.

Fortune quickly lived up to his name. He wrote the group's second No. 1 hit, "Elizabeth," on their 1983 album Today, and followed that with two more No. 1 hits-"My Only Love" (from 1984's Atlanta Blue) and "Too Much On My Heart" (from 1985's Pardners in Rhyme). Fortune also wrote the top-10 hit "Forever" from 1986's Four for the Show and co-wrote the top-10 hit "More Than a Name on the Wall" from 1988's The Greatest Hits. Jimmy has performed in all of the U.S. States, in Canadian Provinces, and in front of audiences as large as 100,000. He was part of the Statlers' annual Happy Birthday USA celebration in Staunton, Virginia, for 14 years. He also sang on many of the Statlers' gold, platinum, and double platinum recordings. Jimmy's career included The Nashville Network's popular "The Statler Brothers Show" which aired for seven seasons and debuted in 1991 as the highest rated show for the network. Jimmy was privileged to perform at the White House on two occasions, once for President Ronald Reagan, and once for President George H. W. Bush. He also presented a special gift to actress Elizabeth Taylor by singing his song "Elizabeth" to her for a birthday celebration.

Jimmy and The Statler Brothers were inducted into the GMA (Gospel Music Association) Hall of Fame on October 29, 2007, and inducted into the CMA (Country Music Association) Hall of Fame on June 29, 2008. Jimmy, as a solo artist, was inducted into the Virginia Musical Hall of Fame in 2018.

After The Statler Brothers retired on October 26, 2002, Jimmy seized the opportunity to launch a solo career to share new music with his fans. His first solo CD, When One Door Closes, was released August 2003 on Audium/Koch. He released a gospel album, I Believe, in June 2005, a Christmas CD, Feels Like Christmas, in 2006, a live concert DVD in 2007 a country CD, "Windows" in 2009, "Lessons" in 2012, and "Hits and Hymns" CD and DVD through Gaither Music Group in 2015 which debuted at #10 Billboard Country Album, #1 Southern Gospel, and #6 Billboard Contemporary Christian. The DVD debuted at #1 on Billboard Music Video charts. In 2017 he recorded a compilation of his favorite songs called "Jimmy Fortune Sings The Classics" on the Gaither Music label. Jimmy is currently living in Nashville, writing, touring, and recording a new project for Gaither Music called "God and Country" set to be released in May of 2019.