2001
Sylvia McNair
Chicago Symphonic Pops Orchestra
Young Artists Performance

2002
Maureen McGovern
St. Louis Brass Quintet
“La Boheme”
New Sousa Band

2003
Glenn Miller Orchestra
Young Artist Gala
“The Merry Widow”
Chanticleer
Kingston Trio

2004
Manhattan Transfer
Gaelic Storm
New Sousa Band
“The Pirates of Penzance”
Duke Ellington Orchestra

2005
A Celebration of Gershwin with Sylvia McNair, Kevin Cole and David Alan Miller and the Milwaukee Symphony Orchestra
The Diamonds
“Cosí fan tutte”
Count Basie Orchestra

2006
Peter Nero and Members of the Milwaukee Symphony Orchestra
The Ramsey Lewis Trio
“The Student Prince”
The Irish Tenors with Arnie Roth and the Chicagoland Pops Orchestra

2007
Five By Design with the Wisconsin Chamber Orchestra
The Blind Boys of Alabama
“The New Moon”
The 5th Dimension

2008
Maureen McGovern and the Chicago Philharmonic Orchestra
The Kingston Trio and The Brothers Four
Prometheus Trio
"Die Fledermaus"
Chicago Brass Quintet
Gordon Goodwin's Big Phat Band with Patti Austin
Kenny Loggins