He has also won twenty three International Bluegrass Music Awards, including winning Resophonic Guitar Player of the Year fifteen times.

[4] As a duo, Ickes and Hensley have performed and recorded with Taj Mahal, Tommy Emmanuel, David Grisman, Molly Tuttle, and Jorma Kaukonen & Hot Tuna.

Ickes has also performed and recorded with a "jamgrass acoustic power trio", Three Ring Circle, with Andy Leftwich and Dave Pomeroy.

He has also collaborated with a wide range of musicians, including Merle Haggard, Earl Scruggs, Tony Rice, Charlie Haden, David Grisman, Alison Krauss, Willie Nelson, David Lee Roth, Dolly Parton, Patty Loveless, Peter Rowan, Niall Toner, Claire Lynch, and Mary Chapin Carpenter and the southern gospel group The Dunaways.

Other notable collaborations include the CD Earl Scruggs with Family & Friends, The Ultimate Collection: Live at the Ryman (2008, Rounder), nominated for the 2009 Grammy for Best Bluegrass Album; and "Earl Scruggs, Doc Watson, Ricky Skaggs, The Three Pickers" (2003, Rounder DVD & CD), which appeared on the Billboard Bluegrass Chart for 138 weeks.

The project featured Clint Eastwood, Jimmy Buffett, Garrison Keillor, Brad Paisley, Sheryl Crow, Vince Gill, Emmylou Harris, and others.