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Widower Anthony Morton "Tony" Micelli is a former baseball player who was forced to retire due to a shoulder injury. He wants to move out of Brooklyn to find a better environment for his daughter, Samantha (Alyssa Milano). He ends up taking a job in upscale Fairfield, Connecticut, as a live-in housekeeper for divorced advertising executive Angela Bower and her son Jonathan. The Micellis move into the Bower residence. Appearing frequently is Angela's feisty, sexually progressive mother Mona Robinson. Mona dates all kinds of men, from college age to silver-haired CEOs. This portrayal of a middle age woman with an active social and sexual life was unusual for television at the time.

The title of the show refers to the clear role reversal of the two lead actors, where a woman is the breadwinner and a man (although he is not her husband) stays at home and takes care of the household. It challenged contemporary stereotypes of Italian-American young males as macho and boorish and wholly ignorant of life outside of urban working-class neighborhoods, as Tony was depicted as sensitive, intelligent and domestic with an interest in intellectual pursuits, and yet still athletic and streetwise.

The easy-going, spontaneous Tony and the driven, self-controlled Angela are attracted to each other, though both are uncomfortable with the notion for much of the run of the show. While there is playful banter and many hints of their feelings for each other, Tony and Angela do their best to avoid facing this aspect of their developing relationship and date other people. Angela has a steady romantic interest in Geoffrey Wells (Robin Thomas), while Tony has a variety of girlfriends who come and go, including Kathleen Sawyer (Kate Vernon) in seasons six and seven. In the meantime, however, they become best friends, relying on each other frequently for emotional support. In addition, Tony provides a male role model for Jonathan, while Angela and Mona give Samantha the womanly guidance she had been missing.

Keeping ties with Tony's and Samantha's Brooklyn roots, motherly former neighbor Mrs. Rossini (Rhoda Gemignani), who ends up becoming a thorn in Mona's side, and several other friends turn up a few times each season, sometimes in New York, sometimes in Connecticut.

Angela eventually strikes out on her own and opens her own ad firm in season three, while Tony decides to go back to school, enrolling in the same college that daughter Samantha would later attend. Samantha's best friend Bonnie (Shana Lane-Block) is a recurring character during these seasons, while romance comes into her life in the form of boyfriend Jesse Nash (Scott Bloom) during her senior year of high school and into college.

At the start of season eight, Tony and Angela finally acknowledge their love for each other. However, the series does not end with the widely expected marriage but on a more ambiguous note. This was due primarily to concerns by the network that a marriage, representing a definitive ending, could hurt syndication. Tony Danza also vehemently opposed the marriage, saying it would contradict the original purpose of the show.[citation needed]

During the final season, Samantha finds a new love in Hank Thomopoulous (Curnal Achilles Aulisio), who became a full-time character in January 1992. A fellow college student, Hank was originally poised to enter a medical program, but soon decides to become a puppeteer. Sam and Hank marry after an engagement lasting a matter of weeks.

Synopsis

Cast

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Judith Light

as

Angela Bower

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Tony Danza 

as 

Tony Micelli

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Katherine Helmond

as 

Mona Robinson

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cast
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Alyssa Milano 

as 

Samantha Micelli 

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Danny Pintauro

as

Jonathan Bower

Guest appearances

Delta Burke appeared in the first season as next door neighbor Diane Wilmington. Betty White also appeared in the first season as television host Bobbie Barnes. Comic James Coco was a frequent guest, beginning in season one as Tony's father-in-law Nick Milano, visiting from New York. People have credited his appearances on Who's the Boss? as a prime example of his comedic abilities on TV, despite the fact that he was not a regular and had never starred in a successful TV series of his own. When Coco died in February 1987, prior to the conclusion of season three, his character was written out as having died as well (with a funeral episode and tribute).

 

By the fall of 1990, with Samantha beginning college and Jonathan in high school, Who's the Boss?, like other series getting on in years, added a new younger cast member. Producers brought in five-year-old Billy (Jonathan Halyalkar), an orphan from the Micellis' old Brooklyn neighborhood whose grandmother left Billy in Tony's care. He moves in with the Bower family in season seven. Billy was a comic foil to Tony, but also attempted to get into the mix in other characters' 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 timing the senior cast members had long established with each other. He was written out of the show at the end of the season. In the beginning of season eight, it was briefly explained that Billy had returned to live with his grandmother.

Frank Sinatra made a guest appearance in a 1989 episode, as well as Ray CharlesMike Tyson and Thomas HearnsLeslie Nielsen played Max, who was engaged to Mona in a 1988 episode. Matthew Perry played Benjamin Dawson, a roommate of Samantha's in a 1990 episode. Robert Mandan guest-starred in two episodes, as a CEO and love interest for Mona; Mandan and Helmond had previously starred as husband and wife in the comedy-drama Soap.

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