- "Sex, Pies and Idiot Scrapes"
- Lucky Jim (Robert Forster), A bail bondsman who meets Homer. He recruits Ned Flanders to hunt Homer down after Homer jumps his bail.
- Wolf the Bounty Hunter (Hank Azaria), a bounty hunter who convinces Homer to take up bounty hunting. A parody of Dog the Bounty Hunter.
- Patrick Farally (Harry Shearer), an Irishman who gives Marge a job at his erotic bakery.
- "Double, Double, Boy in Trouble"
- "Mypods and Boomsticks"
- Bashir Bin Laden (Tress MacNeille), Bart's new friend from Jordan. He almost gets beaten up by the three bullies (Dolph, Jimbo, and Kearney) for being Muslim, and Homer insults his parents and accuse them of being terrorists because of their religion (Islam).
- "Lisa the Drama Queen"
- Juliet Hobbs (Emily Blunt), a strange new girl whom Lisa befriends. Together, the two create a fantasy world called Equalia where the two reign as queens. She runs away from home at the end of the episode it is unknown if she returns home.
- "Take My Life, Please"
- Vance Connor, Homer's old high rival who won the student council election after Principal Dondelinger rigged the election.
- "Wedding for Disaster"
- The Parson (Hank Azaria), A colleague of Rev. Lovejoy, who appears to tell him the during a certain time he was not licensed. He is the titular head of Lovejoy's faith.
- "In the Name of the Grandfather"
- Tom O'Flanagan (Colm Meaney), the owner of O'Flanagan's pub in Dunkilderry, Ireland. Kenneth Branagh had originally been asked guest star as the pub owner and came in to record the part. However, Branagh was replaced by Meaney and did not appear in the episode.
- "Eeny Teeny Maya Moe"
- Maya (Tress MacNeille), is a beautiful woman Moe meets over the internet. When Moe meets her in person, she is three feet tall. Despite this they end up hitting it off, even after Moe worried what his friends/patrons would think of her, to which Homer did not even pay attention to her height. Moe came close to making her Mrs. Maya Szyslak, but got too comfortable joking around with her about her height, much to her chagrin. To make it up to her, he tried to literally knock himself down to her size, but she convinced him not to by leaving him for trying something so insane and insensitive.
- "The Good, the Sad and the Drugly"
- Jenny (Anne Hathaway) is the beautiful girl who Bart fell in love with. At first she thought Bart was a nice guy, but then she dumped him. She helps out around the Springfield Retirement Castle. She's a Christian and prays to God at school. Bart tricked her into believing that he was something he was not which is the reason he got dumped and left by Jenny. Bart has not seen her since.
- Inga (unknown), Groundskeeper Willie's Swedish girlfriend. She is a bikini model who lives in his shack.
- "Waverly Hills 9-0-2-1-D'oh"
- Alaska Nebraska (Ellen Page), a teen pop star based on Miley Cyrus's "Hannah Montana" persona.
Famous quotes containing the word season:
“At Christmas I no more desire a rose
Than wish a snow in Mays new-fangled shows,
But like of each thing that in season grows.”
—William Shakespeare (15641616)
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