Lightcap's first two CDs as a leader, Lay-Up (2000) and Bigmouth (2003) were released on the Fresh Sound New Talent label and featured a quartet line-up with Gerald Cleaver on drums and Tony Malaby and Bill McHenry on tenor saxophones.

[4] Two years later he expanded the group to a quintet, naming it Bigmouth and establishing a line-up of Craig Taborn on keyboards, Chris Cheek and Malaby on tenor saxophones and Cleaver on drums.

[7] Bigmouth's 2015 release on Clean Feed Records, Epicenter features this batch of music along with a cover of The Velvet Underground's "All Tomorrow's Parties".

He received a second CMA New Jazz Works grant in 2016, the result of which was SuperBigmouth (which combined his Bigmouth and Superette bands), released on Pyroclastic Records in 2019.

Lightcap has worked with Marc Ribot, Regina Carter, Craig Taborn, John Medeski, Tomasz Stanko, John Scofield, The Swell Season, Mark Turner, Joe Morris, Chris Potter, Glen Hansard, Sheila Jordan, James Carter, Butch Morris, Ben Monder, Ghost Train Orchestra, Tom Harrell, and others.