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Sam has an on-again, off-again relationship with the bar waitress Diane Chambers (Shelley Long) for the series' first five seasons until her departure from the series.

Then he tries to seduce Diane's replacement, Rebecca Howe (Kirstie Alley), who frequently rejects his advances.

Although his celebrity status was short-lived, Sam retains that standing within the confines of Cheers, where he is beloved by the regular patrons.

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Sam's baseball career declined when he became an alcoholic.

Over time, Sam's role as a bartender turns him into the "resident ringleader for an assortment of poor souls and wanna-be's".

Robert Sutton's (Gilbert Lewis) group meetings for sex addicts, a referral made by Frasier.

In the series finale, "One for the Road" (1993), Sam reunites with Diane after six years of separation.

As well, Martin Crane saw him pitch at the Kingdome, which opened in 1977.

Although his baseball career is not highly detailed throughout the series, Sam was at times a good-to-very-good pitcher (stories of him retiring star batters occur during the series) but not a great one.

In the tenth season (1991–92), they try to conceive a child, but by then they have decided to stay friends.

In "The Guy Can't Help It" (1993), Sam plays with the idea of marrying Rebecca (as a safety net "in case no one better comes along"), but several bar patrons and even Carla tell Sam his womanizing is getting him nowhere, prompting him to join Dr.

In "I Do, Adieu" (episode 121, 1987), Sam and Diane try to marry but call off the wedding to let her start a supposedly promising writing career.

In the following episode "Home Is the Sailor" (episode 122, 1987), Sam sells Cheers to the Lillian Corporation six months before the episode and later returns to the bar to work under employment of the "voluptuously beautiful" In "Cry Harder" (episode 194, 1990), Sam is able to buy back the bar from the Lillian Corporation after Sam has saved the corporation from financial victimization by Robin Colcord (Roger Rees), Rebecca's lover.

Diane finds that out from Coach, and involves her love interest Frasier Crane (Kelsey Grammer) in helping Sam slowly regain his sobriety in the following episode, "Rebound, Part Two".

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