He is a member of the groups Punch Brothers, Mighty Poplar and was previously in Leftover Salmon as well as the John Cowan Band.

Pikelny is a nine-time Grammy Award nominee, winning once in 2019 for Best Folk Album.

In high school, he began studying with Greg Cahill of the Chicago bluegrass band The Special Consensus.

After Thile had a jam session with Witcher, Pikelny, bassist Greg Garrison and guitarist Chris Eldridge, he decided he wanted the band to be a quintet.

[5] After on and off touring throughout 2007 coinciding with Nickel Creek's Farewell (For Now) Tour, the band's name was changed to the "Tensions Mountain Boys" briefly, and subsequently to Punch Brothers (borrowed from a short story by Mark Twain).