Cinninger was raised in Niles, Michigan where he says his parents' extensive record collection influenced his eclectic tastes in music. Cinninger began playing in many bands by the age of 12, ranging in styles from jazz fusion to country music. After spending some time in the Berklee School of Music, he took classical guitar lessons from Gerry Zubko in Roseland, South Bend, Indiana. In 1997, he started his own band, Ali Baba's Tahini and regularly played shows alongside of another local band, Umphrey's McGee. Cinninger chose to learn his chops by playing with others rather than attend a college musical curriculum, as many of his friends did. Eventually, Ali Baba's Tahini disbanded in 2000 and Cinninger accepted an offer to join as a full-time member of Umphrey's McGee in 2000. His first show as a member of the band was on September 1, 2000. Since joining the band, he has, along with founder Brendan Bayliss, become one of the group's main songwriters. In 2001, Cinninger released a self-titled solo album released on the Monkey Fuzz Records label. Several of its tracks developed into Umphrey's McGee songs, such as "Blue Echo," "Utopian Sky" which became "Utopian Fir," and "Aster Heights" which contained parts of "Roulette" and "Last Man Swerving." In 2004, five years after their initial split, Cinninger reformed Ali Baba's Tahini to record an album in the North Carolina mountains.
Guitars
Jake uses a G&L Comanche, G&L S500, G&L ASAT, a G&L S500 deluxe, G&L Legacy, a Fender Stratocaster, a Babicz Identity Series Jumbo Cutaway Acoustic, and various custom Becker guitars. Jake's current touring rig consists mainly of an orange custom shop G&L Legacy, a red G&L commanche, and a custom made 7 string guitar. On tour these guitars are run into a custom schroeder amplification head for clean tones, and a custom OldField head for higher gain tones. He also uses an early '80s Marshall JCM 800, endorses Marshall Vintage Modern amps, OldField amps, and also uses Fuchs Audio Technology, and with Umphrey's McGee endorses Moog synthesizers, Morleyeffects pedals, Source Audioeffect pedals and BBE Sound effects. Jake also incorporates an unusual type of tremolo arm on his G&L guitar. The arm itself is a small piece of metal which is conformed to a specific shape. It is used as a palm rest to actuate the vibrato. This device is called the "Jake Blade" and was custom made. The "Jake Blade" is now available on the Umphrey's Mcgee website in the merchandise section.