Cummings started playing the five-string banjo at the age of twelve when his father's guitar was too big for his hands, and started learning basic chords and progressions, and became a fan of bluegrass music. In his late teens he encountered the early recordings of Stevie Ray Vaughan and was floored by the virtuosity. While in college in 1987 he saw Vaughan perform and he returned to the guitar with a new outlook and resolve. His first public guitar performance came in 1997, when he played at his friends wedding reception. In his late twenties he formed a band, Swamp Yankee, and in 1999 released an independently produced album, The Long Way. The trio spent two hours in a recording studio to record the nine songs for the album. Soon he was on the Northeast blues circuit with his band. In 1998 he walked into a Northeast Blues Society open jam, which led to Cummings’ winning the right to compete in the Blues Foundation's 1999 International Blues Challenge, in Memphis. The following year Albert released his debut recording, The Long Way. Bluesprint magazine said it was “a barrage of guitar pyrotechnics that calls to mind a grand mix of the styles of past masters like Albert King, Freddie King, Stevie Ray Vaughan, and Jimmie Hendrix.” That in turn opened up an opportunity for him to work with Double Trouble, the late Stevie Ray Vaughan's rhythm section. So taken with Cummings's fire and passion were bassistTommy Shannon and drummer Chris Layton that they volunteered to play on and produce his solo debut recording, 2003’s self-released From the Heart. Recorded in Austin, Texas, it featured Cummings fronting Double Trouble in their first recording project since Stevie Ray’s passing. Cummings’ soulful and explosive approach to blues and rock caught the attention of Blind Pig Records, which signed him to a multi-album deal beginning in 2004. Only Shannon remained as the bassist for Cummings' next album. True To Yourself in 2004. Two years later, in 2006, Cummings recorded a fourth album Working Man, with new band members. In 2008, Cummings released a live albumFeels So Good, recorded at the Colonial Theatre in Pittsfield, Massachusetts. a 95-year-old “little jewel box” – that’s what James Taylor calls it – that’s hosted everyone from Will Rogers to Al Jolson. The audience was so enthralled and supportive they became part of the performance in a way that’s rarely heard. As AllMusic put it, “It sounds like it was one hell of a party that night.” In 2011 Albert released an instructional DVD for the Hal Leonard Corporation entitled, Working Man Blues Guitar. His 2012 album No Regrets debuted at No. 1 in the U.S., Canada and France on the iTunes Blues Charts and at No. 5 on the Billboard blues charts. In a 2012 interview, he called No Regrets his "best album yet". In July 2015, Cummings released Someone Like You, a 12-track Blind Pig album produced by David Z. In February 2020, Cummings released his 11-track Provogue Records debut titled Believe, produced by Grammy Award-winning producer Jim Gaines. Recorded at the iconic FAME Studios in Muscle Shoals, Alabama, Cummings notes the influence the location had on the process of creating this project, “If I had recorded those same songs anywhere else, then Believe would have sounded like a completely different album.” Arguably one of the most notable tracks on the album is a cover of the song Hold On by legendary soul duo Sam & Dave, illustrating Cummings' ability to fuse genres while remaining stylistically unique and fresh.
