Homeless Harold (Season 11)

This season ran from September 4, 1999 to May 22, 2000.

Episodes

 * 1022: "The Mafia and the Bad" (September 4, 1999)
 * Guest Stars: James Gandolfini as the mob boss, Alabama 3 as the musical performers of "Woke Up This Morning"
 * 1020: "Pains and Gains" (September 11, 1999)
 * 1019: "The Suckers" (September 18, 1999)
 * 1021: "Groin Impalers" (September 25, 1999)
 * Guest Stars: Ed McMahon as himself
 * 1018: "The Democratic Thieves" (October 10, 1999)
 * Guest Stars: Maurice Lamarche as the Thief
 * 1101: "And Away We Go!" (October 17, 1999)
 * Guest Stars: Natalie Portman and Hayden Christensen as themselves
 * 1015: "The Murdoch Files" (October 24, 1999)
 * Guest Stars: Rupert Murdoch as himself
 * 1102: "Trick Or Tweet!" (October 31, 1999)
 * Guest Stars: Kelsey Grammer as the evil vet
 * 1103: "The Hacksaw Fridge" (November 28, 1999)
 * 1105: "The Shipwreck" (December 20, 1999)
 * Featured Song: "The Aquarium" by Camille Saint-Saens
 * 1104: "Pretty Korman" (January 11, 2000)
 * 1106: "The Suburbs of Treeplestia" (January 25, 2000)
 * 1107: "Jokey Smokey" (February 16, 2000)
 * Guest Stars: Patrick Warburton as Jokey
 * 1108: "The SmackDowners" (March 2, 2000)
 * Guest Stars: Vince McMahon as himself
 * 1111: "This Guy Started A Fuss" (March 9, 2000)
 * 1109: "Love, Not Loathe" (March 16, 2000)
 * Guest Stars: Maurice Lamarche as Dad
 * 1114: "The Red Tricycle" (March 23, 2000)
 * 1117: "The Redemption" (March 30, 2000)
 * 1113: "His Name Was John" (April 6, 2000)
 * 1112: "Kill Phil, Volumes 1 & 2" (April 13, 2000)
 * Guest Stars: Frank Welker
 * 1116: "The Gun Wound" (April 20, 2000)
 * 1118: "Rainbow Go Low" (April 27, 2000)
 * 1110: "The Baby Is All Right" (May 22, 2000)
 * Guest Stars: Buzz Aldrin and Neil Armstrong as themselves
 * Featured Songs: "Sometimes When We Touch" by Dan Hill and "Bad" by Michael Jackson