Rebecca dreams of making love to Sam and is horrified. Sam overhears her confessing her dreams to the Cranes. He uses a cassette tape of the sound of rain in an effort to make her fall asleep, allowing him to seduce her. Unaffected, Rebecca confronts him, foiling the plan. She is close to giving into Sam, however, when multimillionaire Robin Colcord enters the scene and interrupts their lovemaking.

Robin Colcord enters the bar's office to tell Rebecca that, rather than sell a South End property as she suggested in her letters to him, he is developing the property "as an exclusive urban complex". Rebecca accepts Robin's offer to take her to Beverly Hills, California. While they travel around the West Coast, Sam realizes that he cares about her. At the office, Sam is ready to confess his concerns to her but then backs down when Robin seizes the opportunity first, saying that he cares about her "very, very deeply". When Robin leaves, Rebecca reluctantly hints to Sam that she and Robin have not yet made love. She fears that when they do, he will lose interest in her and leave. Sam figures that she finds him more sexually interesting than Robin, which a horrified Rebecca denies.

Sam reevaluates his life and his job as a bartender. When the gang lifts his spirits, Norm suggests that Sam use a loan to buy an old abandoned bar that went bankrupt a year earlier. Initially the gang is skeptical due to the bar's dilapidated condition, but then realize some parts of it remain intact and undamaged. The following day, Robin inspires Sam to come up with the idea of turning a whole block, and the abandoned bar, into newer buildings, including a high-rise. Robin tells Sam he cannot afford the block. He encourages Sam to say what he really wants, which is to buy back Cheers. The following day, Robin tells Sam that he has already bought the whole block to develop Sam's idea (for which Robin takes credit). Sam feels cheated.

Cliff's old flame Margaret O'Keefe (Annie Golden) returns from Canada to offer him a committed relationship, which literally blinds him. Frasier theorizes that Cliff's hysterical blindness is caused by his fear of commitment. Sam explains the situation to Maggie. She feels bad and decides to return to Canada. Cliff stops her and declares his commitment to her. Meanwhile, Rebecca crashes into a plastic surgeon's car. Instead of reporting her, he offers her surgery, which she accepts, having an old tattoo and her mole (disguised by the tattoo) removed.

Norm hires workers for his painting business, with which he has been preoccupied. Rather than boss them around, Norm lets them slack off. Tired of being exploited, Norm invents a nonexistent business partner named "Anton Kreitzer". While Norm continues the charade, the workers become tired of Kreitzer's treatment of them. Sam drives Norm in a used Volaré—a replacement for his Corvette, which he sold to Lilith to earn money to buy back Cheers—to Norm's business. They arrive just before the workers who have come to confront "Kreitzer". Norm goes into "Kreitzer"'s office—actually, the back alley filled with garbage—and confronts him telling him that he will take the workers and form a new business. The workers scold Norm for upsetting "Kreitzer", however, and reject his offer. A few hours later one of the workers, Rudy (Eric Allen Kramer), returns to Kreitzer's office only to discover the charade. While Frasier orders Lilith to return the Corvette to Sam, Rudy confronts Norm, assuming that Norm is truly "Kreitzer", and quits. Norm fails to convince Rudy otherwise.

Rebecca invites Boston Mayor Raymond Flynn to Cheers' centennial anniversary party. The mayor meets Cliff and has him arrested for sending him threatening letters. Then he almost presents a plaque indicating the bar's landmark status. However, Lilith feels labor pains since she is two weeks overdue. Having witnessed the event, Flynn withholds the plaque and leaves the bar. Frasier's car has been towed, so Sam uses his Corvette to take Frasier and Lilith to a hospital. They discover that the pains are simply contractions. Sam and Frasier help another woman give birth. Lilith is discharged but then gives birth to a son named Frederick in a taxicab and then is sent back to the hospital.

Carla receives news that her husband Eddie died when he fell into an ice resurfacer while he was saving an ice show performer from it. At Eddie's funeral, when the name "Mrs. LeBec" is announced, Carla and another woman named Gloria (Anne De Salvo) stand up to discover they are both married to Eddie. The women argue and then fight, leading to a brawl. Later, Gloria enters the bar. She tells Carla that like her, she also has twins. Carla feels that Eddie must have loved Gloria more than her. Soon, Gordie Brown (Thomas Hayden Church), the man Eddie saved, arrives. He gives Carla a letter Eddie gave to him a few months earlier. It says that he felt guilty for hiding the truth from Carla about impregnating and secretly marrying Gloria, and that Carla has been the love of his life. Gordie does not have a letter for Gloria, disappointing her. Rather than let Gloria take a bus home, Carla allows her to stay at her house for the time being.

To honor her Jewish faith, Frasier and Lilith decide to circumcise their newborn son Frederick at a scheduled bris. Frasier reconsiders after witnessing the graphic nature of the ritual and takes Frederick to Cheers. Lilith enters the bar and convinces Frasier to allow the ceremony to continue. Rebecca has trouble enlivening a retirement party in the billiard room for a very dull corporate employee—Larry (Jay Robinson). She organizes a wet T-shirt contest in an effort to do so, but the contest becomes depressing when the models tell their sad stories. Jaded, Rebecca allows Frederick's bris to take place in the billiard room at the same time. Consequently, the retirement party livens up, and Larry plans to marry one of the models. Meanwhile, Carla petitions to have her late husband Eddie's Boston Bruins number retired to honor him. Despite her efforts, including forging signatures, the hockey team's executives refuse to retire the number but give her season tickets to the Bruins' games instead.

Woody is cast as George, one of leading roles in a community theater production of Our Town, alongside highly praised actress Emily, (Lisa Kudrow), cast as the character of the same name. However, Woody has trouble performing love scenes convincingly with Emily. At the bar, Kelly walks into the billiard room to see Woody and Emily kissing while rehearsing a love scene. Kelly realizes that Woody kept his leading role a secret. Woody admits he did this because he felt that Kelly would be uncomfortable seeing him kiss another woman in a play. Then Woody tells Kelly that he loves her. When he fails to convincingly say the same thing to Emily, Emily tells him the director will replace him if he is not convincing in the love scene. Woody immediately says "I love you" to Emily and realizes that fear is a key to successful acting. Meanwhile, Cliff wins the bar's beard-growing contest through cheating.

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In this episode, Frasier tells patrons that his father was neglectful and a busy scientist before he died. In Frasier his father Martin is a retired cop and alive. This contradiction is clarified in "The Show Where Sam Shows Up".

Frustrated that Robin spends little time with her, Rebecca sneaks into his apartment to surprise him. Sam, told by Carla about Rebecca's plans, goes to the apartment to seduce her after learning Robin will be late. When she tries to kick Sam out, Rebecca accidentally activates Robin's security system, which also locks the elevator doors and windows. Sam and Rebecca spend the night talking briefly and then sleeping. The next morning, when the system is deactivated, they leave the apartment without being seen by anyone. Meanwhile, Frasier is aghast to see other players "lie, steal, and cheat" while playing Monopoly. Norm tells him that they were teaching Woody about the harsh side of the economy (which Woody was curious about in the beginning).

Norm's painting business flounders. He fires his secretary Doris, (Cynthia Stevenson), giving her a letter of recommendation. Mistaking it as a love letter, she becomes infatuated with and then stalks Norm. He eventually rehires her to return things to normal. Robin delivers an antique desk to Rebecca containing a paper hinting at a "ring". She assumes it is an engagement ring. A deliveryman then gives Sam a box that fell from the desk. It contains a certificate of authenticity revealing that writer George Bernard Shaw previously owned the desk. The "ring" is a dark circle "visible on the desktop" where Shaw set his tea cup. The desk's value contains a five and many zeros, i.e. is very high. Rebecca is disassembling the desk, however, still unaware of the actual "ring". Woody obsesses over a weather record and wins a trip to Hawaii—actually, one of the show's tricks^[14]—on a radio contest with his knowledge.

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Cynthia Stevenson first appeared as Doris in the episode "The Two Faces of Norm".

Robin receives a fax from his bauxite miners saying that he must either negotiate or face a wildcat strike action at midnight. He lends Sam his sailboat for a race whose grand prize is $10,000. If he wins, this would give Sam another opportunity to buy back Cheers. Sam chooses Carla and Norm as his crew. During the race they discover a time bomb in the boat's refrigerator. The boat's radio is already disassembled, sharks are swimming around the boat, and the inflatable lifeboat has been sabotaged. Running out of options, they manage to sail to an inlet and escaped to shore before the boat exploded. Later in the bar, when Robin arrives from his meeting, he offers Sam the opportunity to sign release forms to share Robin's insurance policy and then offers him $60,000. Sam declines them both, to Carla and Norm's dismay.

Rebecca invites one of her professors, Alice Anne Volkman (Alexis Smith), for dinner at Melville's. Sam tags along to discuss with Volkman how to buy back Cheers. The following day, Volkman tells Rebecca that she and Sam slept together at a hotel. Infuriated, Rebecca orders Sam to end the relationship. Later, at the office, Volkman tells her they slept together again at the same hotel, prompting Rebecca to call her a "slut". Volkman praises Rebecca for expressing her own opinions without worrying about offending others. Meanwhile, Carla is audited by the IRS, so she forges multiple receipts.

Cliff appears on Jeopardy!, performing well. For the final Jeopardy clue, "Archibald Leach, Bernard Schwartz and Lucille LeSueur", he wagers $22,000 and loses it by responding incorrectly: "Who are three people who've never been in my kitchen?" Cliff objects and argues, demanding that his answer be accepted. The show's host, Alex Trebek, later arrives at Cheers, tells Cliff that his response should have been accepted, and announces his resignation as host. Cliff convinces Trebek to stay by telling him how much he and Jeopardy mean to him. When Cliff leaves the scene, Trebek reveals to Norm that the story about quitting the show was a fabrication to placate, Cliff who scares him. Meanwhile, Sam discovers that a thief stole his "little black book" and has been impersonating him to make dates he never shows up for. After investigating, the thief is revealed a teenage boy who wants to become a "babe hound" like Sam. Letting him go, Sam tells the boy to start as a "babe pup", to call girls around his age, and gives him $25 for a haircut.

While heading to a dinner party, Robin and Rebecca start to make love in his limo. The following day, the fulfilled Rebecca takes the gang to Little Wally's Pup 'n' Burger, where Robin took her the night after the party, to hang out. Later at Little Wally's, when Rebecca goes to the women's restroom to clean a stain from her clothes, Sam sees Robin with another woman going to Little Wally's.

At Little Wally's, to prevent Rebecca from finding out about Robin and another woman, Sam uses his jacket to cover her head while they run from a nonexistent fire. The following day, Robin offers Sam the ownership of Cheers just to silence him about the affair. When she plans to move into Robin's apartment, Sam tells Rebecca the whole truth about Robin. Rebecca does not believe him until she meets one of Robin's women named Christine Devi in his limousine. The two women confront Robin, who admits that he also has a chargé d'affaires (diplomat) as a third woman. While Christine breaks up with him, Rebecca makes love again with Robin in the limo. Later at the bar, Rebecca tells Sam that she is considering breaking up with Robin. Then Robin arrives to give her a diamond bracelet as a gift. She initially rejects it, but when Robin considers giving it to the chargé d'affaires yet puts Rebecca in the lead for her "standards", Rebecca takes the bracelet and continues to go out with him.

Kelly's divorced mother, Roxanne (Melendy Britt), invites Woody to her sister's wedding rehearsal dinner. While everyone else is having hors d'oeuvres, in another room Roxanne kisses Woody, terrifying him. Sam, also invited by Kelly, spends $1,000 on a stockbroker's company stock that turns out to be worthless. Woody loudly rejects Roxanne's advances in front of the guests, humiliating Kelly. Later at the bar, Kelly apologizes to Woody on behalf of Roxanne, who has flirted with Kelly's previous boyfriends, which she passes off as mere "innocent flirts". Then Kelly gives him Roxanne's letter, which, unbeknownst to Kelly, is a love letter. After Kelly leaves, Woody reads the letter and passes it off as a joke. Meanwhile, Cliff has been stuck on a bankrupt restaurant's mechanical bull for hours in the billiard room and wants to get off it. When firefighters cover the walls with mattresses so he can safely get off the bull, the bar patrons insist he stay on for five more hours to break the world record.

A talk show host brings Lilith's invited guests Sam (bad boy) and Frasier (good boy) to the stage as examples for Lilith's latest book Good Girls, Bad Boys, much to Lilith's chagrin. Sam impresses the female guests, while Frasier fails to do so. Lilith inadvertently becomes infatuated with, and then kisses, Sam. Later, Frasier questions himself whether he is too much of a "good boy", so he begins dating a female motorcyclist who then offers him a ride to Florida. He declines and reconciles with Lilith. Meanwhile, the gang teases Cliff over his fears of suffering from side effects, like enlarged breasts, while taking medication to relieve job stress.

Robin spends his day off competing with Sam at darts and pool. Sam wins the games. Robin chooses chess, which he considers more intellectually challenging, as the next game to play. While they are playing, the bar patrons assist Sam using a chess game on Rebecca's computer and a transmitter. The computer goes out, putting Sam at a disadvantage. Despite this, he makes a few moves that help him win without their assistance. However, Robin reveals that he knew Sam was cheating, so he teasingly awards him a penny. Rebecca, disappointed that Robin did not spend his entire day with her, confronts the pair about their behavior. However, Sam and Robin then play a thumb war, disappointing Rebecca again.

Carla and Eddie's other widow Gloria (Anne De Salvo) get along well. Carla receives a letter from the ice show company naming her the beneficiary of Eddie's $50,000 accident policy. Carla plans to break her promise to split Eddie's estate with Gloria. When she becomes suspicious that Gloria knows about the money, Carla reluctantly gives her half of the settlement. Gloria is ungrateful. Despite this, Carla feels that she did the right thing. Meanwhile, Woody is cast in a revival of Hair, which includes a nude scene. Worried, Woody goes topless at the bar for practice. During the opening night show, Woody appears nude, but is the only actor to do so, embarrassing himself.

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John Ratzenberger does not appear in this episode, though Cliff is briefly mentioned.

St. Patrick's Day is unusual at Cheers. Cliff is reluctant to discuss trivial matters. Norm feels full after drinking enough beers that do not taste normal as before. Then the gang notices that the bar's wooden statue of Tecumseh is missing. Their rival Gary is the suspected culprit. Sam, Norm, and Cliff pose as city workers and close Gary's Olde Towne Tavern due to nonexistent toxic waste. Soon, the statue of Tecumseh returns; Rebecca reveals that she sent it to be revarnished. Fearing Gary's retaliation, Sam, Norm, Cliff, and Woody have their hair cut spelling Gary's name one letter on each head. However, the gang realizes that Sam has been wearing a fake bald cap to cover his hair. Rebecca enters the scene and reveals the Tavern has been closed for renovations for a month and Gary has been in Florida. While the gang wants to get even with Gary, they first chase after Sam to cut his hair.

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In this episode, Frasier claims that both his parents are dead. However, his father Martin turns up alive in Frasier. The inconsistency is clarified in the episode "The Show Where Sam Shows Up".

Woody gives his father's promise ring to his girlfriend Kelly, who is to be sent away to Europe. When Woody makes insulting remarks about her father Walter (Richard Doyle), she returns the ring to him. To make up, Woody goes to the Gaines' manor and climbs up a ladder, with Sam's assistance, to Kelly's room. He proposes they elope. When Walter arrives, Woody hides in her closet and then overhears Kelly and Walter sharing their father-daughter moment together, prompting him to back down from the idea and allow Kelly to go to Europe. Meanwhile, Norm is discovered not to have put his name into a hat for the first drawing for the "designated driver" contest. The bar patrons vengefully write Norm's name for a new draw, making him the driver and keeping him from drinking.

While Sam stays home recovering from chickenpox, Carla goes out with a Boston Red Sox player, Darryl Mead (Kevin Conroy), only to see visions of her dead husband Eddie LeBec in an ice hockey uniform. Frasier suggests that she see a psychiatrist; instead, she invites psychic Madame Lazora (Georgia Brown) to channel Eddie's spirit. When Madame Lazora performs a séance, a skeptical Frasier angrily calls the process a "sham". Carla argues with Frasier, saying that she believes in Madame Lazora and she has probably conjured up images of Eddie because she fears going out on her first date since Eddie's death. Madame Lazora claims that Eddie's spirit says that Carla was right, irritating Frasier. Carla pays her $250 for the 15-minute session, feels that she made peace with Eddie, and happily decides to continue dating Darryl. Meanwhile, Rebecca appears on a talk show Consumer Patrol to complain about a defective leg shaving device. She rescinds her complaint when she realizes that a company owned by her love interest, Robin Colcord, made the product.

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Ted Danson was forced to skip filming for this episode due to chickenpox. Danson only has a brief appearance in the cold open that was filmed separately following his recovery.

Kevin Conroy first appeared as Darryl Mead in "Death Takes a Holiday on Ice."

Robin and the chargé d'affaires, named Jeanne-Marie, are supposed to attend a ball in Boston. Rebecca sends Sam to spy on them. The following day, Sam tells Rebecca he had sex with Jeanne-Marie in an elevator. This did not happen because the ball was cancelled due to a broken water pipe. Rebecca insists Sam show her what Jeanne-Marie did that made her such a good lover. They go to the elevator where Rebecca leaves Sam tied up and half-naked. Woody chooses a woman named Terry (Christine Cavanaugh) as his roommate to cover the increased rent for his apartment. He meets Terry's husband, Cutter Gardner (Eric Bruskotter), to whom Terry wants to return. Woody points out Cliff as Terry's "roommate" just to have jealous Cutter chase after Cliff. Lilith sings "Sonny Boy" as Frederick's lullaby, impressing Frasier and the bar patrons who were skeptical about her singing.

Robin buys his lover Jeanne-Marie a new house and invites Rebecca to move in with him. Rebecca enlists Sam and Norm to move furniture into it while Robin is in Zürich to surprise him. They discover Robin's papers revealing classified information about Rebecca's company, Lillian Corporation, also Robin's competitor. They realize that Robin has hacked into Rebecca's company computer using her secret password, "Sweet Baby", since the day after they first made love, part of Robin's hostile takeover plan. The following day, Rebecca goes to the Lillian Corporation, planning to show Robin's papers to the board of directors. Robin arrives, having returned from Zürich, and proposes marriage to Rebecca. She accepts. Robin then snatches his papers from Sam, who is holding them while trying to convince her to reconsider, and Robin shreds them with his portable shredder. After Robin and Rebecca leave, one of the corporate executives tells Sam the board is suspicious of Rebecca, who will be reported to authorities. To protect her, Sam names Robin as the main culprit.

Robin, indicted for insider trading, is bailed out because of his clean record. As a reward for turning Robin in, an executive of the Lillian Corporation offers Sam the opportunity to buy back Cheers for $1. Without money on him, Sam collects eighty-five cents from others, which the executive accepts as the official purchase amount. Furious about Sam's involvement, Rebecca plans to quit Cheers and follow Robin, who has jumped bail and fled the United States on his private jet. She receives Robin's fax saying, "Goodbye forever", which devastates her. The following day, she receives a letter from her company saying that she is fired. Sam hires Rebecca as a waitress. At night, she splashes drinks on male customers. Sam confronts her in the office about her recent behavior and her failures in life. Then Sam and Rebecca make love. At closing time, Robin arrives, returning from abroad, having realized that he loves her. He is aghast to find Sam and Rebecca together in the office.

The special is book-ended by the gang watching it at Cheers. It also includes an extended sequence of young Woody Boyd's experience touring the haunted mansion at Disneyland.

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Aired as an episode of the Wonderful World of Disney. Sketches included the Jungle Cruise ride, The Muppets, Ernest, and Will Smith.

The gang (minus Carla) are watching the events happening on the Earth Day Special, and discuss ways they can help the environment.

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The Earth Day Special was hosted by real-life husband and wife, Rhea Perlman and Danny DeVito, thus Carla does not appear in the Cheers segment they are watching.