As a trombonist, Jeff Callaway has recorded or performed with John Hiatt, Bobby Rush, Jim Dickinson, Jim Gaines, Charley Pride, Dorothy Moore, Marty Stuart, Pinetop Perkins, Paul Overstreet, Nanette Workman, the Williams Brothers, Eddie Cotton, Brandy, The Tommy Dorsey Orchestra, The Temptations, The Four Tops, The Bo-Keys (featuring Skip Pitts, Willie Hall, Scott Bomar, Jim Spake, Marc Franklin), The Hemptones, Dent May, The Vamps, Patrick Smith Band, Duff Dorrough, Taylor Grocery Band, Afrissippi, Blue Mountain, The Kudzu Kings, The Sincere Ramblers, Willie Clayton, Keith "WonderBoy" Johnson, The Actual Tigers, Charlie Mars, Fabian, James Darren, Bobby Rydell, The Neckbones, The Preachers Kids, Kenny Brown, Joyce Cobb, Bonerama, K.C. Ray, Harvey Scales, Bobby Patterson, Fillmore Slim, The Bluz Boys, The Capitol City Stage Band, The Dee Barton Orchestra, John Sinclair, The Herman Green Machine with Calvin Newborn Jr., The Supernatural, Freeworld, Soul Pocket, Larry, Gilmore, Enigma Jazz Project, Bensenville (IL) Wind Ensemble, Guy Hovis, Stars Over Mississippi Orchestra (backing Nell Carter, Debbie Allen, Phil Hartman, Kathy Ireland, Ann Margaret, Mary Ann Mobley, Gary Collins, Marilu Henner), The Ole Miss Marching Band and The Mississippi Symphony Orchestra, among others.

A frequent performer heard statewide on the Oxford Mississippi-based Thacker Mountain Radio, he recently appeared on John Hiatt's  Master of Disaster and is currently preparing to release his debut solo multi-instrumental album, By Landlord's Request. He holds music degrees from Ole Miss and VanderCook College of Music in Chicago, and in 2003 was elected into the Ole Miss Jazz Alumni Hall of Fame.