AllMusic critic MacKenzie Wilson has called Reynolds "an under-rated master".

[2][3] Reynolds plays the guitar, piano, sitar, drums, violin, bass, keyboards, ethnic percussive instruments, solo djembe, harp, uses drum machines for special effects, and sings,[4] although his performances are primarily instrumental rock music.

However, his older sister owned some albums from the Beatles, which he says, even as a very young child, he loved instantly, playing air guitar to their music.

Upon reaching adolescence, Reynolds learned guitar and bass guitar, so he could perform in the family's local church choir three times a week,[1] while also beginning to experiment with learning what eventually became second nature: adding riffs infused with rock and roll, funk and soul music by the age of twelve.

Later landing in Charlottesville, Virginia, finding jazz, jazz fusion, and experimental music enthusiasts there, Reynolds found the college town a more welcoming environment for him to branch out musically than any of his previous homes, and added to his experimentation other musical influences to his repertoire, including sixties psychedelic rock, citing some of his early influences as Jimi Hendrix, Carlos Santana and Led Zeppelin.

[1] By the 1990s, he had formed the Tim Reynolds Three, or TR3, and had added other influences, such as Nine Inch Nails, Bob Marley and Marilyn Manson.

After a few years these shows gained popularity, and in 1996 Matthews and Reynolds embarked on their first full tour together as a duo.

In 2008, Reynolds once again joined Dave Matthews Band for the recording of Big Whiskey and the Groogrux King with producer Rob Cavallo.

[7] Reynolds and Matthews performed together several times in April 2008: in support of Presidential candidate Barack Obama,[8] at the "Seeds of Compassion" show in Seattle[9] and at Jack Johnson's Kokua Festival at the Waikiki Shell on the island of Oahu, in Hawaii.

[10] Reynolds toured as lead guitarist with the Dave Matthews Band in support of Big Whiskey and the GrooGrux King in early 2008.

Most of Some Devil was played live that tour, along with a wide variety of covers, including, by Reynolds' request, Peter Gabriel's hit "Solsbury Hill".

[17] On 4 October 2009 Reynolds performed with Matthews in St. Louis, Missouri to support Farm Aid in 2009 [18] and again in Hartford, Connecticut on 22 September 2018.