Homeless Harold (Season 21)

This season aired from October 3, 2009 to May 23, 2010.

Episodes

 * 2017: "The Celebrity Secrets" (October 3, 2009)
 * Guest Stars: Julia Roberts, Jude Law, Winona Ryder, Betty White, Dwayne Johnson, Scarlett Johansson, Brad Pitt, Leonardo DiCaprio, Elton John, Stan Lee, Justin Timberlake, Ron Howard, Bryce Dallas Howard, Angelina Jolie, Sigourney Weaver, Annie Potts, J.K. Simmons, Natalie Portman, Judd Apatow, Jermaine Dupri, and Jagged Edge as themselves, and Maurice LaMarche as the narrator
 * Note: Due to the extensive amount of celebrity guest stars appearing in this episode, it was extended to 45 minutes.
 * 2016: "The Joke Dare" (October 10, 2009)
 * 2014: "Son Of A Gun" (October 17, 2009)
 * 2015: "Fandemonium" (October 24, 2009)
 * 2020: "The Halloweenized 20th Anny Special" (October 31, 2009)
 * Guest Stars: Ray Romano as Frankenstein, Kelsey Grammer as the evil vet
 * 2019: "The Flu of Terios" (November 21, 2009)
 * Guest Stars: Jason Bateman as Terios
 * 2018: "The Weirdness" (November 28, 2009)
 * 2101: "ADHD 2.0" (December 5, 2009)
 * Guest Stars: Daniel Radcliffe as Jack
 * 2102: "The Difficult Decision" (December 19, 2009)
 * Guest Stars: Emma Watson as herself
 * 2103: "Sucky Ducky" (December 19, 2009)
 * 2104: "G.O.D" (January 9, 2010)
 * 2105: "WWE... Is Not What You Think It Is!" (January 16, 2010)
 * Guest Stars: Vince McMahon, Stephanie McMahon, Triple H, Dusty Rhodes, John Cena, Shane McMahon, Kane, The Undertaker, and Beth Pheonix as themselves, and Maurice LaMarche as the Narrator
 * Note: Second documentary themed 45 minute episode in Season 21.
 * 2107: "Gays Go Along" (January 30, 2010)
 * 2106: "Erica" (February 13, 2010)
 * Guest Stars: Natalie Portman as Erica
 * 2109: "The Duke of Swapmabottoms" (February 20, 2010)
 * Guest Stars: Rik Mayall as the Duke
 * 2111: "Dreadlocks Are Banned" (March 6, 2010)
 * Guest Stars: Kel Mitchell as Ragga
 * 2110: "Trademarking Industry" (March 13, 2010)
 * 2108: "The Rockstars" (March 27, 2010)
 * Guest Stars: Ozzy Osbourne as himself, Jude Law as Dr. Adam Gibson
 * 2112: "The Scam" (April 14, 2010)
 * Guest Stars: Kelsey Grammer as Rick Spall
 * 2114: "Born Again John" (April 21, 2010)
 * 2113: "The Secret Entrance" (May 9, 2010)
 * 2115: "Cutback: The Fourth Adventure" (May 23, 2010)
 * Guest Stars: Dwayne Johnson as Cutback, Harrison Ford as Fred Sellers, Keira Knightley as Cutback's wife, Jude Law as Dr. Adam Gibson