31 Dec 1999 - Universal Amphitheatre, Universal City, CA, USA
Main: Fruitcakes, Stars on the Water by Rodney Crowell, Coconut Telegraph, Volcano, Pencil Thin Mustache, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Party Time by Club Trini, Why Don't We Get Drunk, Somewhere Over China, The City by Mac McAnally, Brown Eyed Girl by Van Morrison, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Auld Lang Syne by [traditional], Margaritaville, Lawyers, Guns and Money by Warren Zevon, You Can't Always Get What You Want by The Rolling Stones
11 Dec 1999 - Coral Sky Amphitheatre, West Palm Beach, Florida, FL, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, Pencil Thin Mustache, Boat Drinks, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Migration, Growing Older but Not Up, Tin Cup Chalice, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Fruitcakes, Another Saturday Night by Sam Cooke, Ho Ho Ho and a Bottle of Rhum
9 Dec 1999 - Coral Sky Amphitheatre, West Palm Beach, Florida, FL, USA
Main 1: Lage Nom Ai, Gravity Storm, Ringling, Ringling, Pencil Thin Mustache, Boat Drinks, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Gypsies in the Palace
Main 2: Presents to Send You, That's What Living Is to Me, Trying to Reason With Hurricane Season, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Bob Robert's Society Band, Brown Eyed Girl by Van Morrison, Oysters and Pearls
7 Dec 1999 - Compaq Center, Houston, TX, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, Pencil Thin Mustache, Boat Drinks, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Gypsies in the Palace
Main 2: Migration, Brahma Fear, Who's the Blonde Stranger?, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Coconut Telegraph, Fruitcakes, Pacing the Cage by Bruce Cockburn
4 Dec 1999 - New Orleans Arena, New Orleans, LA, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, Pencil Thin Mustache, Boat Drinks, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, The Pascagoula Run
Main 2: The Wino and I Know, In the Shelter, Grapefruit - Juicy Fruit, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Sea Cruise by Huey "Piano" Smith, Brown Eyed Girl by Van Morrison, Louisiana 1927 by Randy Newman
2 Dec 1999 - Orlando Arena, Orlando, FL, USA
Main 1: Lage Nom Ai, Gravity Storm, Ringling, Ringling, Pencil Thin Mustache, Boat Drinks, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Gypsies in the Palace
Main 2: Migration, That's What Living Is to Me, Brahma Fear, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Brown Eyed Girl by Van Morrison, Fruitcakes, Oysters and Pearls
30 Nov 1999 - Ice Palace, Tampa, FL, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, Pencil Thin Mustache, Boat Drinks, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Presents to Send You, Chanson Pour Les Petits Enfants, Stories We Could Tell by John Sebastian, Coast of Marseilles by Keith Sykes, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Fruitcakes, Coconut Telegraph, Pacing the Cage by Bruce Cockburn
20 Nov 1999 - Bay Street Theater, Sag Harbor, NY, USA
Main: The Weather Is Here, Wish You Were Beautiful, Boat Drinks, Presents to Send You, Grapefruit - Juicy Fruit, Lone Palm, Life Is Just a Tire Swing, Brahma Fear, Morris' Nightmare, Miss You So Badly, Jolly Mon Sing, Banana Republics by Steve Goodman, God's Own Drunk by Lord Buckley, This Old Man, Twelve Volt Man, Door Number Three, Distantly In Love, Migration, Son of a Son of a Sailor, Margaritaville, Southern Cross by Crosby, Stills & Nash
4 Sep 1999 - Tweeter Center, Mansfield, MA, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, Pencil Thin Mustache, Coconut Telegraph, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Looking Back by Mac McAnally, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Love And Luck, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Johnny B. Goode by Chuck Berry, Uncle John's Band by Grateful Dead, Oysters and Pearls
2 Sep 1999 - Tweeter Center, Mansfield, MA, USA
Main 1: Lage Nom Ai, Gravity Storm, Ringling, Ringling, Grapefruit - Juicy Fruit, Coconut Telegraph, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Looking Back by Mac McAnally, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Flesh and Bone, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Math Suks, Love And Luck, Pacing the Cage by Bruce Cockburn
31 Aug 1999 - Meadows Music Theater, Hartford, CT, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, Grapefruit - Juicy Fruit, Coconut Telegraph, Volcano, School Boy Heart, Waiting for the Next Explosion, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Looking Back by Mac McAnally, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Flesh and Bone, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Math Suks, Love And Luck, Oysters and Pearls
28 Aug 1999 - Merriweather Post Pavilion, Columbia, MD, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Pencil Thin Mustache, Grapefruit - Juicy Fruit, Coconut Telegraph, Volcano, Waiting for the Next Explosion, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Looking Back by Mac McAnally, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Love And Luck, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Math Suks, Another Saturday Night by Sam Cooke, Oysters and Pearls
26 Aug 1999 - Merriweather Post Pavilion, Columbia, MD, USA
Main 1: Lage Nom Ai, Gravity Storm, Ringling, Ringling, Grapefruit - Juicy Fruit, Coconut Telegraph, Volcano, Pencil Thin Mustache, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Looking Back by Mac McAnally, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Waiting for the Next Explosion, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Math Suks, Fruitcakes, Pacing the Cage by Bruce Cockburn
23 Aug 1999 - Polaris Amphitheater, Columbus, OH, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, Waiting for the Next Explosion, Coconut Telegraph, Volcano, Grapefruit - Juicy Fruit, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Looking Back by Mac McAnally, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Flesh and Bone, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Math Suks, Love And Luck, Oysters and Pearls
21 Aug 1999 - Riverbend Music Center, Cincinnati, OH, USA
Main 1: Lage Nom Ai, Gravity Storm, Ringling, Ringling, Waiting for the Next Explosion, Coconut Telegraph, Volcano, Pencil Thin Mustache, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Looking Back by Mac McAnally, It's My Job by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Flesh and Bone, Fins, A Pirate Looks at Forty, Club Manhattan by Jesse Winchester, Margaritaville, One Particular Harbour
Encore: Johnny B. Goode by Chuck Berry, Another Saturday Night by Sam Cooke, Oysters and Pearls
19 Aug 1999 - Riverbend Music Center, Cincinnati, OH, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Peanut Butter Conspiracy, Waiting for the Next Explosion, Coconut Telegraph, Volcano, Grapefruit - Juicy Fruit, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: Looking Back by Mac McAnally, He Went to Paris, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Math Suks, Johnny B. Goode by Chuck Berry, Pacing the Cage by Bruce Cockburn
24 Jul 1999 - New World Music Theater, Tinley Park, IL, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, Waiting for the Next Explosion, Volcano, Coconut Telegraph, Pencil Thin Mustache, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: It's My Job by Mac McAnally, Peanut Butter Conspiracy, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, The Pascagoula Run, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Sweet Home Chicago by Robert Johnson, Another Saturday Night by Sam Cooke, Pacing the Cage by Bruce Cockburn
22 Jul 1999 - New World Music Theater, Tinley Park, IL, USA
Main 1: Lage Nom Ai, Gravity Storm, Peanut Butter Conspiracy, King of Somewhere Hot, Coconut Telegraph, Volcano, Pencil Thin Mustache, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: The Ass and the Hole by Mac McAnally, Semi-True Stories by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Waiting for the Next Explosion, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Fruitcakes, Sweet Home Chicago by Robert Johnson, Pacing the Cage by Bruce Cockburn
20 Jul 1999 - Riverport Amphitheater, Maryland Heights, MO, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Ringling, Ringling, King of Somewhere Hot, Coconut Telegraph, Volcano, Pencil Thin Mustache, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: It's My Job by Mac McAnally, He Went to Paris, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, Waiting for the Next Explosion, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Math Suks, Johnny B. Goode by Chuck Berry, Oysters and Pearls
17 Jul 1999 - Alpine Valley Music Theatre, East Troy, WI, USA
Main 1: Lage Nom Ai, Stars on the Water by Rodney Crowell, Peanut Butter Conspiracy, Coconut Telegraph, Waiting for the Next Explosion, Volcano, Pencil Thin Mustache, School Boy Heart, Changes in Latitudes, Changes in Attitudes, Son of a Son of a Sailor, Come Monday, I Will Play for Gumbo, Brown Eyed Girl by Van Morrison
Main 2: The Ass and the Hole by Mac McAnally, Semi-True Stories by Mac McAnally, Why Don't We Get Drunk, Southern Cross by Crosby, Stills & Nash, Cheeseburger in Paradise, Cairo by Johnny Candoso, The Pascagoula Run, Fins, A Pirate Looks at Forty, Margaritaville, One Particular Harbour
Encore: Math Suks, Another Saturday Night by Sam Cooke, Pacing the Cage by Bruce Cockburn