McEntire started playing drums at age 10. Throughout high school, he performed in marching bands and studied privately for seven years. He went on to attend Oberlin Conservatory initially as a percussion major, but eventually switched to study in the school's then newly created program for Technology in Music and Related Arts.
McEntire is currently a member of Tortoise, The Sea and Cake, and The Red Krayola. His drumming work as a sideman can be heard on recordings, such as Since by Richard Buckner, Enantiodromia and Life on the Fly by Azita, Near-Life Experience by Come, Kernel by Seam, Chicago Wednesday by Jandek, and The Spectrum Between by David Grubbs.
While attending Oberlin, he briefly played with Mark Edwards in My Dad Is Dead in 1988, and then joined Bastro with David Grubbs and Bundy K. Brown in 1989. In 1991, he relocated along with Grubbs and Brown to Chicago where they changed their musical direction and became the first incarnation of Gastr Del Sol. Their debut album, The Serpentine Similar, was released in 1993. McEntire and Brown left to play in Tortoise in 1994, yet McEntire continued to make contributions to Gastr Del Sol's later recordings and performances.

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