Homeless Harold (Season 20)

This season ran from August 20, 2008 to May 11, 2009.

Episodes

 * 1920: "Rich and Richer" (August 20, 2008)
 * Guest Stars: Ben Stiller as Sir George Pikes
 * 1914: "Drake On A Train" (September 24, 2008)
 * Guest Stars: Drake as himself
 * 1915: "The Halloween Tale" (October 8, 2008)
 * Guest Stars: Maurice Lamarche as Vincent Price
 * 1917: "The Cross Pains" (October 29, 2008)
 * Guest Stars: Kanye West as himself
 * 1918: "Summer Strummer" (November 5, 2008)
 * Guest Stars: Tom Petty as himself
 * 1916: "The Mystery" (November 19, 2008)
 * Guest Stars: Hugo Weaving as John Dole
 * 1921: "Wait for It" (November 26, 2008)
 * 1919: "The Internet Is Your Witness" (December 10, 2008)
 * Guest Stars: Hayden Christensen as the Internet
 * 1922: "The Mystery of the Yeti Man" (January 15, 2009)
 * Guest Stars: Harold Ramis as the Yeti Man
 * Note: Last ever SD episode.
 * 2001: "Cutback III" (February 5, 2009)
 * Guest Stars: Dwayne Johnson as Cutback, Keira Knightley as Cutback's wife, and Clive Owen as The Zoner
 * Note: First ever HD episode.
 * 2002: "Back to the Present" (February 12, 2009)
 * 2003: "The Waste" (February 19, 2009)
 * 2004: "Old and Decrepit" (February 26, 2009)
 * 2005: "The Secret Land" (March 5, 2009)
 * Guest Stars: Adam West as the Landlord
 * 2006: "Padoop!" (March 12, 2009)
 * 2007: "Jump In Here!" (March 19, 2009)
 * 2008: "The Life of Crime" (March 26, 2009)
 * Guest Stars: Lisa Kudrow as Officer Jane Danielson
 * 2009: "2009" (April 2, 2009)
 * 2010: "Never Wanna Give You Up" (April 9, 2009)
 * Guest Stars: Rick Astley as himself
 * 2011: "The Chopper Life" (April 16, 2009)
 * 2012: "Nifty Business" (April 30, 2009)
 * Guest Stars: Eddie Murphy as himself
 * 2013: "When The Germans Rise" (May 11, 2009)
 * Guest Stars: Brad Pitt as Fredienreich Bunderbaße