- Back Country ShuffleMusic by Pat DonohuePerformed by Pat Donohue & Richard A. Dworsky (as Richard Dworsky)
- Atlanta TwilightMusic by Richard A. Dworsky (as Richard Dworsky)Performed by The Guys All-Star Shoe Band
- Smooth TalkerMusic by Pat Donohue & Richard A. Dworsky (as Richard Dworsky)Performed by Pat Donohue & Richard A. Dworsky (as Richard Dworsky)
- Guy NoirMusic by Richard A. Dworsky (as Richard Dworsky)Lyrics by Garrison KeillorPerformed by The Guys All-Star Shoe Band
- I Used To Work In ChicagoMusic by Garrison KeillorLyrics, TraditionalPerformed by Woody Harrelson & John C. Reilly
- Ladies At The RiverMusic by Richard A. Dworsky (as Richard Dworsky)Performed by Richard A. Dworsky (as Richard Dworsky)
- Go Tell Aunt GladysTraditional: "Go Tell Aunt Rhodie"Additional Lyrics by Garrison KeillorPerformed by Meryl Streep & Lily Tomlin
- PiscacadawadaquoddymogginMusic by Robin WilliamsLyrics by Garrison Keillor
- Tishomingo BluesMusic & Lyrics by Spencer WilliamsPerformed by Garrison Keillor and The Guys All-Star Shoe Band with Robin Williams (as Robin) & Linda Williams
- Independence RagMusic by Pat Donohue & Andy SteinPerformed by The Guys All-Star Shoe Band
- Jens Jensen's Herring CommercialMusic: "Won't You Come Home Bill Bailey"Written by Hughie Cannon (uncredited)Additional Lyrics by Garrison Keillor
- Blues At The FitzMusic by Pat DonohuePerformed by Pat Donohue
- Strappin' The StringsMusic by Andy SteinPerformed by The Guys All-Star Shoe Band
- Slow Days Of SummerMusic & Lyrics by Garrison KeillorPerformed by Garrison Keillor and The Guys All-Star Shoe Band with Robin Williams (as Robin) & Linda Williams
- Softly And TenderlyMusic & Lyrics by Will L. Thompson (as Will Thompson)Performed by Meryl Streep & Lily Tomlin
- MudslideMusic by Pat DonohuePerformed by The Guys All-Star Shoe Band
- Grandfather's ClockMusic & Lyrics by Henry Clay WorkPerformed by The Guys All-Star Shoe Band
- Old Plank RoadMusic & Lyrics by Robin Williams (as Robin) & Linda WilliamsPerformed by Robin Williams (as Robin) & Linda Williams and The Guys All-Star Shoe Band
- My Minnesota HomeMusic: "The Old Folks At Home" by Stephen FosterAdditional Lyrics by Garrison KeillorPerformed by Meryl Streep, Lily Tomlin and The Guys All-Star Shoe Band
- Beboparebop Rhubarb PieTraditional: "Shortnin' Bread"Additional Lyrics by Garrison KeillorPerformed by Garrison Keillor, Meryl Streep and The Guys All-Star Shoe Band
- Guy's ShoesMusic & Lyrics by Pat DonohuePerformed by The Guys All-Star Shoe Band
- You Have Been A Friend To MeMusic & Lyrics by A.P. Carter
- Coming Down From Red LodgeMusic by Peter OstroushkoPerformed by The Guys All-Star Shoe Band with Peter Ostroushko
- Whoop-I-Ti-Yi-YoTraditionalAdditional Lyrics by Garrison KeillorPerformed by Woody Harrelson & John C. Reilly and The Guys All-Star Shoe Band
- Baby, Baby, Be My ManMusic by Richard A. Dworsky (as Richard Dworsky)Lyrics by Garrison KeillorPerformed by Kathy Mueller and Richard A. Dworsky (as Richard Dworsky)
- When The Bloom Is On The SageMusic & Lyrics by Howard Wright (as Fred Howard Wright) & Nat Vincent (as Nathaniel Hawthorne Vincent)Performed by Garrison Keillor and Lindsay Lohan
- Gold Watch & ChainMusic & Lyrics by A.P. CarterPerformed by Garrison Keillor, Meryl Streep and The Guys All-Star Shoe Band with Robin Williams (as Robin) & Linda Williams
- Rollin' In My Sweet Baby's ArmsMusic & Lyrics by Lester FlattPerformed by The Guys All-Star Shoe Band
- Duct Tape UnderscoreMusic by Richard A. Dworsky (as Richard Dworsky)Performed by Richard A. Dworsky (as Richard Dworsky)
- She Is More To Be Pitied Than CensuredMusic & Lyrics by William B. GrayPerformed by Woody Harrelson & John C. Reilly
- Let Your Light Shine On MeTraditional, Arranged by Blind Willie JohnsonPrudence Johnson and The Guys All-Star Shoe Band
- Coffee JingleMusic by Kate MacKenzie & Garrison KeillorLyrics by Garrison KeillorPerformed by Garrison Keillor, Jearlyn Steele and The Guys All-Star Shoe Band
- The New Munich Beer CommercialTraditional: "There Is A Tavern In The Town"Additional Lyrics by Garrison KeillorPerformed by Garrison Keillor, Robin Williams (as Robin) & Linda Williams and The Guys All-Star Shoe Band
- The Day Is ShortMusic by Garrison Keillor & Richard A. Dworsky (as Richard Dworsky)Lyrics by Garrison KeillorPerformed by Jearlyn Steele and The Guys All-Star Shoe Band
- The Prince Of Pizza CommercialMusic: "La donna e mobile" by Giuseppe VerdiAdditional Lyrics by Garrison KeillorPerformed by Garrison Keillor and The Guys All-Star Shoe Band
- A Bunch Of GuysMusic & Lyrics by Richard A. Dworsky (as Richard Dworsky)Performed by The Guys All-Star Shoe Band
- Summit Avenue RagMusic by Richard A. Dworsky (as Richard Dworsky)Performed by The Guys All-Star Shoe Band
- Goodbye To My MamaMusic & Lyrics by Garrison KeillorPerformed by Meryl Streep, Lily Tomlin and The Guys All-Star Shoe Band
- Bad JokesMusic & Lyrics by Garrison KeillorPerformed by Woody Harrelson, John C. Reilly and The Guys All-Star Shoe Band
- Waitin' For YouMusic by Pat DonohuePerformed by The Guys All-Star Shoe Band
- Frankie & JohnnyTraditionalAdditional Lyrics by Garrison KeillorPerformed by Lindsay Lohan and The Guys All-Star Shoe Band
- Red River ValleyTraditionalPerformed by Cast and The Guys All-Star Shoe Band
- While Ye MayMusic by Kevin KlineLyrics by Robert HerrickPerformed by Kevin Kline
- In The Sweet By And ByMusic & Lyrics by S. Fillmore Bennett (as Sanford Bennett) & J.P. Webster (as Joseph Phillbrick Webster)Performed by Cast and The Guys All-Star Shoe Band
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