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The Best Episodes of Who's the Boss? Season 2

Every episode of Who's the Boss? Season 2 ranked from best to worst. Discover the Best Episodes of Who's the Boss? Season 2!

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A former professional baseball player, along with his preteen daughter, moves into New York advertising executive Angela Bower's house to be both a housekeeper and a father figure to her young son. Tony 's laid-back

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Episode Rankings

  1. #1 Fan Favorite
    Who's the Boss? Season 2 Episode 25 - The Anniversary Show
    8.3/10(135 votes)

    S2:E25

    Angela had planned a special dinner for five, in honor of Tony and Samantha's two-year anniversary in Connecticut, but Tony is the only one who doesn't have other plans. During the meal, Tony falls ill and is rushed to the hospital in need of surgery. After he has been given sedatives, but just before he falls asleep, he says ""I love you"" to Angela.

    Director:Asaad Kelada
    Writers:Robert Sternin, Prudence Fraser

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  2. Who's the Boss? Season 2 Episode 17 - Jonathan Plays Cupid
    8.2/10(129 votes)

    S2:E17

    Jonathan's friend gets him worrying that, one day, Tony may no longer be part of his life. Hoping to ensure against Tony leaving, Jonathan arranges for him and Angela to meet on Valentine's Day at a restaurant for a romantic dinner for two. But they think that the ""Mr. Bower"" behind this evening is really Michael, Angela's ex-husband.

    Director:Asaad Kelada
    Writer:Unknown

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  3. Who's the Boss? Season 2 Episode 16 - The Babysitter
    8.0/10(126 votes)

    S2:E16

    A sitter's last-minute cancellation leaves Samantha to watch Jonathan while Angela and Tony go to a parents' meeting at school. Samantha panics when Jonathan inadvertently tosses a piece of jewelry down the sink drain. Although Tony had told her not to have any guests, the house is soon full of her friends: Chad, a boy who thinks he can retrieve the missing jewelry, and four of Samantha's friends who come to admire Chad. Tony and Angela return home just as the kids are sneaking out.

    Director:Asaad Kelada
    Writer:Unknown

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  4. Who's the Boss? Season 2 Episode 1 - It Happened One Summer (1)
    7.9/10(155 votes)

    S2:E1

    The family visit Jonathan's summer camp when his counselor calls Angela to say he is homesick. While there, Angela and Tony realize they both attended camp in the same area many years earlier. Their individual stories of their first kiss seem to coincide, and they soon suspect they may have met each other a long time ago.

    Director:Asaad Kelada
    Writer:Blake Hunter

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  5. Who's the Boss? Season 2 Episode 2 - It Happened One Summer (2)
    7.9/10(158 votes)

    S2:E2

    After visiting the site in the woods where each remembers from their past, a thunderstorm prevents Tony and Angela from returning to the campsite in time. They end up having to share a room at a cheap hotel. Meanwhile, Mona and the campers tell scary stories and play pranks on the counselor.

    Director:Asaad Kelada
    Writer:Blake Hunter

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  6. Who's the Boss? Season 2 Episode 6 - Custody (1)
    7.9/10(133 votes)

    S2:E6

    Michael, Angela's ex-husband, returns to announce he is going to be married again soon, and invites everyone to California for the wedding. Jonathan takes an instant liking to Heather, his father's new wife-to-be, and to the California lifestyle. Michael tells Angela that he thinks their son would have a better life in California, and that he wants custody of Jonathan.

    Director:Asaad Kelada
    Writers:Robert Sternin, Prudence Fraser

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  7. Who's the Boss? Season 2 Episode 7 - Custody (2)
    7.9/10(128 votes)

    S2:E7

    While everyone prepares for the wedding, Angela and Michael plan for a legal battle for custody of Jonathan. Soon, Angela is ready to give up, but a messy incident at the ceremony proves to Michael and Heather that they are not ready to be parents.

    Director:Asaad Kelada
    Writers:Robert Sternin, Prudence Fraser

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  8. Who's the Boss? Season 2 Episode 8 - Hunk of the Month
    7.8/10(132 votes)

    S2:E8

    After posing for a calendar, Tony becomes the object of a seductive woman's affections. Angela doesn't want him to date her, but her views change when one of the calendar's other stars takes an interest in her.

    Director:Michael Zinberg
    Writer:Unknown

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  9. Who's the Boss? Season 2 Episode 9 - Thanksgiving at Mrs. Rossini's
    7.8/10(132 votes)

    S2:E9

    The family go to Mrs. Rossini's apartment for Thanksgiving. Angela is disgusted by the antiquated custom of women waiting on men, hand and foot. She also feels threatened by one of the guests, an attractive young girl who used to know Tony and is interested in him romantically. Meanwhile, Mona appears in the Macy's Thanksgiving Day Parade as one of Santa's elves.

    Director:Asaad Kelada
    Writer:Unknown

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  10. Who's the Boss? Season 2 Episode 4 - The Heiress
    7.7/10(131 votes)

    S2:E4

    The family is thrilled when a recently deceased stranger leaves Mona a sizable chunk of money in his will. Mona soon realizes who the man was, and suddenly doesn't want the money. The man turns out to be a former family friend with whom Mona had an affair many years ago.

    Director:Unknown
    Writer:Unknown

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  11. Who's the Boss? Season 2 Episode 24 - The Unnatural
    7.7/10(126 votes)

    S2:E24

    One of Tony's old baseball friends visits and the two end up in a competition to organize a team of players, then play each other. Tony wants to have Angela play for his team, but when he turns out to be a demanding coach, she decides to play for the other team.

    Director:Jim Drake
    Writer:Unknown

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  12. Who's the Boss? Season 2 Episode 14 - Educating Tony
    7.6/10(122 votes)

    S2:E14

    Angela is teaching a class on advertising, and Tony is one of her students. For the students' first assignment, they are to make a commercial for a laundry detergent. Tony is overbearingly proud of his ad, but Angela despises it and give him an F.

    Director:Asaad Kelada
    Writer:Michael Poryes

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  13. Who's the Boss? Season 2 Episode 18 - When Worlds Collide
    7.6/10(124 votes)

    S2:E18

    Tony's poker game has run late, and Angela hurries him to clean up the house in time for her friend who will soon be arriving. Just as his last guest (a raucous Brooklynite) is ready to leave, Angela's friend (a quiet, straight-laced woman) arrives, and the two end up as an item.

    Director:Asaad Kelada
    Writer:Unknown

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  14. Who's the Boss? Season 2 Episode 3 - Ad Man Micelli
    7.5/10(134 votes)

    S2:E3

    Samantha has just begun junior high school, and has little trouble becoming friends with the popular girls. Since they are all from wealthy families, Samantha is afraid they will not like her if they know of her true past, so she tells them that Tony owns Angela's house and is an advertising executive.

    Director:Asaad Kelada
    Writers:Robert Sternin, Prudence Fraser

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  15. Who's the Boss? Season 2 Episode 10 - The Prodigal Father-in-Law
    7.5/10(120 votes)

    S2:E10

    Nick, Samantha's grandfather, is denied parole from prison, so he breaks out and prepares to run from the law. First, though, he must confront Samantha, who refuses to speak to him for what he is doing.

    Director:Asaad Kelada
    Writer:Unknown

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  16. Who's the Boss? Season 2 Episode 21 - Not with My Client, You Don't
    7.5/10(114 votes)

    S2:E21

    A wealthy international client of Angela's sends his daughter to handle his affairs. She takes a liking to Tony, who agrees to be her escort. But Angela soon feels that she forced the woman on Tony, and goes to break them up.

    Director:Asaad Kelada
    Writer:Unknown

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  17. Who's the Boss? Season 2 Episode 12 - Tony the Nanny
    7.4/10(124 votes)

    S2:E12

    A distant relative of Tony's comes to town to meet the man she is to marry through an arranged marriage. Upon learning that the intended groom is a male chauvinist, Tony throws him out of the house and forbids him to marry his cousin. But this infuriates her father, who flies from Italy to confront Tony.

    Director:Katherine Helmond
    Writer:Unknown

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  18. Who's the Boss? Season 2 Episode 13 - Junior Executive
    7.4/10(128 votes)

    S2:E13

    When Samantha needs more money to participate in activities with her basketball team, Angela hires her to work for her on Saturdays. But Samantha soon realizes that, by working weekends, she is missing all the events she wanted money for. So she decides to do a poor job, hoping to get fired.

    Director:Unknown
    Writer:Unknown

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  19. Who's the Boss? Season 2 Episode 22 - Angela's New Best Friend
    7.4/10(126 votes)

    S2:E22

    Arrogant, obnoxious neighbor Diane is devastated by her husband's recent decision to leave her for their maid. She temporarily moves in with the Bowers and Micellis, and nobody in the family enjoys her company.

    Director:Asaad Kelada
    Writer:Unknown

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  20. Who's the Boss? Season 2 Episode 5 - Tony the Matchmaker
    7.3/10(127 votes)

    S2:E5

    Wally, a recently dumped friend of Tony's, is down on his luck, so Tony convinces Angela to go out with him. She is not interested in seeing him again, until Mona dates him. Then a mother-daughter rivalry begins for Wally's attention

    Director:Asaad Kelada
    Writer:Unknown

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  21. Who's the Boss? Season 2 Episode 19 - Losers and Other Strangers
    7.3/10(119 votes)

    S2:E19

    Tony is excited about his bowling trophy. But his victory is overshadowed when Angela, who was quite certain she would win an advertising award for which she'd been nominated, comes home empty-handed. Tony suggests that Angela might feel better about her loss if she congratulated the winner.

    Director:Asaad Kelada
    Writer:Unknown

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  22. Who's the Boss? Season 2 Episode 20 - Tony for President
    7.3/10(119 votes)

    S2:E20

    Tony's campaign for PTA president is clouded by his opponent's mudslinging. He attempts to justify her accusations by explaining some past misunderstandings (this is done through clips of earlier episodes).

    Director:Asaad Kelada
    Writer:Howard Meyers

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  23. Who's the Boss? Season 2 Episode 11 - The Graduate
    7.2/10(113 votes)

    S2:E11

    Recent college graduate Mona is asked to secretly participate in a sting against age discrimination by applying for a job, then getting turned down. But when Angela learns that her mother has this job interview, she pulls some strings to get Mona hired.

    Director:Asaad Kelada
    Writer:Unknown

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  24. Who's the Boss? Season 2 Episode 15 - Gotta Dance
    7.0/10(115 votes)

    S2:E15

    Tony signs up Samantha for ballet lessons. He is pleased when her instructor tells him she has great potential, but the compliment may not have been sincere.

    Director:Asaad Kelada
    Writer:Howard Meyers

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  25. Who's the Boss? Season 2 Episode 23 - There's No Business Like Shoe Business
    6.2/10(120 votes)

    S2:E23

    After hearing a colleague from the shoe factory describe his boredom with his life, Mona encourages him to be spontaneous and pursue a new life. He takes her advice a little too far when he leaves his wife and infant in search of Hollywood stardom.

    Director:Asaad Kelada
    Writer:Unknown

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Season 2 Ratings Summary

"The Anniversary Show" is the best rated episode of "Who's the Boss?" season 2. It scored 8.3/10 based on 135 votes. Directed by Asaad Kelada and written by Robert Sternin, Prudence Fraser, it aired on 5/6/1986. This episode is rated 0.1 points higher than the second-best, "Jonathan Plays Cupid".