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- 1999–6.8 (7)TV Episode
- DirectorPamela FrymanStarsCharlie SheenJon CryerAngus T. JonesAfter Jake flips off his teacher, Alan and Judith move to punish him. Charlie, meanwhile, has other plans for Jake's teacher. Chaos ensues when Jake discovers the relationship and the increasingly overbearing Miss Pasternak tells Charlie she believes God brought them together.
- 2003–201522mTV-147.3 (1.4K)TV EpisodeDirectorPamela FrymanStarsCharlie SheenJon CryerAngus T. JonesEvelyn announces she is receiving an honor from the real estate industry and that Charlie and Alan will host a party in her honor. Mayhem ensues when Berta and her sister agree to cater the event, but sibling rivalry takes center stage.
- 2003–201522mTV-147.7 (1.2K)TV EpisodeDirectorJames WiddoesStarsCharlie SheenJon CryerAngus T. JonesCharlie is suffering from a bad cold, and Rose suddenly and mysteriously resurfaces to "take care of him." So why isn't Charlie getting any better?
- 2003–201522mTV-147.8 (1.4K)TV EpisodeDirectorGary HalvorsonStarsCharlie SheenJon CryerAngus T. JonesA freak food-flinging accident leaves Alan with impaired vision, which doesn't bode well especially when he draws a liking to one of Charlie's exes.
- DirectorPamela FrymanStarsCharlie SheenJon CryerAngus T. JonesAn old classmate is in town while Charlie and Alan spar over whom she likes more.
- DirectorBob SweeneyStarsBob CraneWerner KlempererJohn BannerA disagreeable Russian pilot wants to escape, but refuses to go first to London. He wants to head east to Mother Russia.
- DirectorLee Shallat ChemelStarsMichael J. FoxCarla GuginoRichard KindDr. Bronsteen, an old professor of James', is appointed the city's new School Commissioner by Winston, but it is later revealed by the press that he was caught on camera smoking pot at a 1971 Grateful Dead concert causing duress for Mike and disbelief for James. Ashley is offered a job reporting for a local TV station.
- 2003–201521mTV-147.8 (1.4K)TV EpisodeDirectorPamela FrymanStarsCharlie SheenJon CryerAngus T. JonesAfter one of her ex-husbands dies, Evelyn summons Alan, Charlie, and Jake to the funeral, where Charlie takes a keen interest in the widow.
- DirectorRob SchillerStarsKevin JamesLeah ReminiVictor WilliamsThings get out of hand as Doug frantically tries to stop a woman who claims to have spent a romantic weekend with him from calling the house.
- DirectorRob SchillerStarsKevin JamesLeah ReminiVictor WilliamsDoug, Deacon, Danny and Spence are headed for Memphis so Spence can tell Denise, who's about to get married, they belong together.
- 2003–201522mTV-148.3 (1.5K)TV EpisodeDirectorGary HalvorsonStarsCharlie SheenJon CryerAngus T. JonesAlan is made to admit to Charlie, who keeps hitting it in, he has hit rock-bottom now that his brainless girlfriend Kandi has moved in with his ex. It's all so confusing that Jake would prefer dad's ladies to be lesbians, then tells him Kandi's mom Mandi has joined Charlie's endless list of sexual conquests. Alan can't talk to Kandi, she just repeats Judith's phrases, clearly without understanding the words, but he sees her dad, Mandi's ex Andy, arrive on blind date with his own ex Judith. Frolicking finale at Judith's, in rooms, bed and hot-tub.
- DirectorLee Shallat ChemelStarsMichael J. FoxRichard KindAlan RuckMike plans a star-studded party for the Mayor's 50th birthday, but tries to keep him away from Holly Cohen, Randall's romantic interest from the governor's office so that the Winston marriage doesn't suffer.
- DirectorBob SweeneyStarsBob CraneWerner KlempererJohn BannerPosing as waiters, the heroes want to get rid of a room full of German generals.
- 2003–201521mTV-148.4 (1.9K)TV EpisodeDirectorAndrew D. WeymanStarsCharlie SheenJon CryerAngus T. JonesCharlie's old flame Jill visits and has really changed: she had an operation and is now called "Bill." Before Charlie can adapt, Evelyn meets and starts dating Bill.
- DirectorJerry ZaksStarsCharlie SheenJon CryerAngus T. JonesAlan turns to Jake's teacher for stimulating conversation, since Kandi obviously can't provide any. But the teacher starts to get the wrong idea about Alan's intentions.
- DirectorRob SchillerStarsKevin JamesLeah ReminiVictor WilliamsOn Valentine's Day, Carrie has to cancel dinner with Doug because he and Deacon have to deliver 2 penguins to Albany.
- DirectorMichael J. WeithornStarsKevin JamesLeah ReminiVictor WilliamsDoug, Deacon, Spence and Danny all secretly rent an apartment, but soon Deacon, Spence and Danny move out and Doug lives by himself. Carrie tries to sell a condo to Kirstie Alley but it turns out to be more work than she expected.
- 2003–201520mTV-147.9 (1.6K)TV EpisodeDirectorAndrew D. WeymanStarsCharlie SheenJon CryerAngus T. JonesCharlie is offended when Alan chooses their married, responsible cousins as Jake's guardians.