Living… in Boston, with his mother. They first lived in Cliff’s childhood two-story house, but that was bulldozed after his mother sold it to a convenience-store builder. After that they moved to a condominium, where he crashed on a sofabed. Cliff’s living situation is a constant source of amusement for (and disdain from) his cohorts at Cheers, his local tavern and second home.
Profession… postal worker. Cliff brings a great deal of pride and self-importance to his job and becomes annoyed anytime someone slights it. He likens it to being part of the police force and sees himself as an integral, irreplaceable part of the nation’s fabric. It’s an honest, blue-collar living, in stark contrast to his father’s enterprises as a fraudster constantly running into trouble.
Interests... trivia. Cliff either has or feigns expertise on almost any subject, annoying most everyone around him with his windbaggery. The real test of his knowledge came when he got onto Jeopardy!, amassing a dominating lead before losing it all in Final Jeopardy. He was practically guaranteed a win, but his hubris got the best of him as he wagered – and lost – everything.
Relationship Status... unlucky in love. Cliff carried a torch for Diane, the erudite waitress and sometime girlfriend of Cheers owner Sam Malone, until Cliff made a pass and was thoroughly rejected and kicked out of his own car. He’s had a few short-lived relationships, the most prominent being with fellow postal worker Margaret O’Keefe. Margaret complimented his eccentricities perfectly and revealed Cliff’s deeper side. When she became pregnant with another man’s child, he was willing to stay by her side as a stepfather, until she eventually returned to the child’s biological father.
Challenge… gaining the respect of others. Cliff is always trying to impress the patrons of Cheers with his storehouse of useless trivia, but he mostly ends up annoying them. He is completely transparent in his attempts to shoe-horn irrelevant factoids into on-going conversations, to the point where even the staff insults him. He’s socially awkward and generally ignored by women. Nothing ever fully works out for Cliff, but he keeps trying.
Personality... know-it-all. Cliff talks a big game, yet rarely delivers when under pressure. He is obsessed with how he’s perceived and desperately wants the approval of others. It’s hard to take him seriously because of how badly he wants to be taken seriously. He’s the resident butt-of-jokes because it’s almost too easy to make fun of him, with his living situation and lack of sex life. But if Cliff suddenly vacated his Cheers barstool, even his most bitter antagonists (hello, Carla Tortelli) would quickly discover that they miss him. Cliffie just kind of grows on you.
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