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Widower Tony Micelli (Danza) is a former second baseman for the St. Louis Cardinals who was forced to retire due to a shoulder injury and the up and coming career of Tommy Herr. He wanted to move out of Brooklyn to find a better environment for his daughter, Samantha (Alyssa Milano). He ended up taking a job in upscale Fairfield, Connecticut as a live-in housekeeper for divorced advertising executive Angela Bower (Judith Light). The Micellis moved into the Bower residence. Also starring were Danny Pintauro as Angela's son Jonathan and Katherine Helmond as Mona Robinson, her feisty, man-hungry mother.

The title of the show referred to the clear role reversal of the two lead actors, where a woman was the breadwinner, while a man stayed at home and took care of the house, thus the question of who the "boss" really was. It challenged media stereotypes of Italian-Americans as wholly ignorant of life outside of urban working-class neighborhoods.

The contrast between easy-going, spontaneous Tony and driven, self-controlled Angela resulted in their mutual attraction. While there was playful banter and many hints of attraction for much of the run, Tony and Angela never consummated the relationship, and dated others. Angela had a steady man in Geoffrey Wells (Robin Thomas), while Tony had many girlfriends who came and went, including Kathleen Sawyer (Kate Vernon) in seasons six and seven. Finally at the start of the eighth season, Tony and Angela admitted their love for each other, and had a whirlwind romance until the end of the series. They presumably got married after the last episode.

In addition, Tony provided a much-needed male role model for geeky Jonathan, while Angela (and even Mona) gave Samantha the woman's guidance she had been missing.

Keeping ties with Tony's and Samantha's Brooklyn roots, former motherly neighbor Mrs. Rossini (Rhoda Gemignani) turned up a few times each season, whether visited by the cast in New York or by way of her coming to Connecticut. One of her very important appearances was in the Christmas episode of season two, in which Tony's childhood apartment was up for rent, causing Tony, Mrs. Rossini, and some other relatives to retrieve furniture and Micelli family possessions. Tony's final time in the apartment brought back serious memories of his late father, and how they were angry at each other when he died. Tony confided in Angela about his regret over not making up with him, but it was Mrs. Rossini who livened spirts for the Christmas season. Danza said later that this episode was based on a real-life experience with his own father, who had died on bad terms with him while Danza was starring on Taxi.

Amid the surroundings of prosperity between Angela and Mona (who eventually opened up their own ad firm together in the third season), Tony decided to go back to school, enrolling in the same college daughter Samantha attended in 1988. Samantha's best friend Bonnie (Shana Lane-Block) was a recurring character during these seasons, while steady romance came into her life in the form of boyfriend Jesse Nash (Scott Bloom) during her senior year of high school and into college.

By the fall of 1990, with Samantha in the middle of college and Jonathan in high school, Who's the Boss?, like other series getting on in years, fell victim to the infusion of a new "cute child" to the cast. For the seventh season, producers added 5-year-old Billy (Jonathan Halyalkar), a kid from the Micellis' old Brooklyn neighborhood, who seemed to move into the household but actually frequently visited. Billy was a comic foil to Tony, but also attempted to get into the mix in other character's storylines. He only lasted that season however. In the E! True Hollywood Story about the series, Katherine Helmond remarked that Halyalkar was a gifted performer but had difficulty catching up to the pace of the acting and writing that had been set by the cast and crew for several seasons.

In the fall of 1991, after more or less seven years on its established Tuesday night slot, Who's the Boss? was moved to Saturday nights, along with fellow long-running sitcom Growing Pains. Originally suspected by the insiders that the move was due to the show's waning popularity on Tuesdays and Wednesdays (respectively), ABC attempted to diffuse this fact by adding another long-running show with somewhat higher ratings, Perfect Strangers, to the Saturday lineup in February 1992. All three shows, along with the new cartoon Capitol Critters, launched the new I Love Saturday Night lineup - an equivalent to the hit Friday TGIF lineup. While Perfect Strangers saw a record ratings drop due to the move, Who's the Boss? (as well as Growing Pains) had been falling lower than ever all season, which led to the ultimate decision to end the series - while "some people were still watching". The hour-long series finale aired Saturday April 25, 1992, along with the finales for Growing Pains and MacGyver, which only aired on that night for its final show, even though it still aired on Mondays for its last season.

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