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The Best Episodes of Who's the Boss?

Every episode of Who's the Boss? ranked from best to worst. Let's dive into the Best Episodes of Who's the Boss?!

Binge this in 3d 3h•Peaking at 8.3/10

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

    #1 - The Anniversary Show

    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 8 Episode 1 - Seer of Love
    8.3/10(118 votes)

    #2 - Seer of Love

    S8:E1

    Angela is ready to profess her love for Tony, but her hopes for a romantic anniversary night with him are dashed when he invites her and the whole family to a carnival. A fortune teller tells Tony that he is about to lose the love of his life, but he misses the point. A ride through the Tunnel Of Love changes their relationship.

    Director:Unknown
    Writer:Unknown

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

    #3 - Jonathan Plays Cupid

    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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  4. Who's the Boss? Season 3 Episode 16 - Hit the Road, Chad
    8.2/10(129 votes)

    #4 - Hit the Road, Chad

    S3:E16

    Samantha thinks her boyfriend Chad is the cat's meow when he writes a song just for her. Word gets around, and the tune is heard by legend Ray Charles whom Angela cooerses into recording it for her ad agency. When rat Chad starts seeing another girl, Samantha is so infuriated she demands the recording not take place. It takes a stellar performance of the song by Ray to make Samantha see that her friendship with Angela is more important than getting back at Chad.

    Director:Asaad Kelada
    Writer:Howard Meyers

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  5. Who's the Boss? Season 4 Episode 23 - Sleep Talk, Sweet Talk
    8.2/10(120 votes)

    #5 - Sleep Talk, Sweet Talk

    S4:E23

    One year has passed and it's again Angela's birthday. In the nights after she has found out about the surprise party Tony gives, she talks in the sleep and confesses that she loves Tony. But waking up all with her 'Tony, Tony' shouts is, however, very embarrassing for her.

    Director:Asaad Kelada
    Writer:Unknown

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  6. Who's the Boss? Season 8 Episode 24 - Savor the Veal (3)
    8.2/10(128 votes)

    #6 - Savor the Veal (3)

    S8:E24

    Angela attempts to adjust to her new life in Iowa, but discovers that she really wants to be back east, working at her agency. The conflict of professional interest threatens to split up Tony and Angela.

    Director:Unknown
    Writers:Danny Kallis, Bob Rosenfarb

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    The 20 WORST Episodes of Who's the Boss?

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  7. Who's the Boss? Season 1 Episode 22 - First Kiss
    8.0/10(164 votes)

    #7 - First Kiss

    S1:E22

    Angela comes home from a rowdy birthday party, just as Tony returns home from a police-sponsored demonstration of the effects of alcohol on the mind. Both are in a woozy state, and they end up kissing.

    Director:Asaad Kelada
    Writers:Robert Sternin, Prudence Fraser

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

    #8 - The Babysitter

    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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  9. Who's the Boss? Season 4 Episode 1 - Frankie and Tony Are Lovers
    8.0/10(130 votes)

    #9 - Frankie and Tony Are Lovers

    S4:E1

    At a street carnival in Brooklyn Tony and Angela help at Mrs. Rossini's stand. There Tony also meets Frankie, an old friend. At an charity auction - Tony offers his services for a weekend - she makes the race.After the weekend Tony returns with a proposal from Frankie.

    Director:Asaad Kelada
    Writer:Unknown

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  10. Who's the Boss? Season 4 Episode 7 - A Farewell to Nick
    8.0/10(135 votes)

    #10 - A Farewell to Nick

    S4:E7

    Sam is invited by her grandfather to visit him in Florida. But on her way there, Nick dies. First Sam tries to pay no attention to this but Nick's death, however, left big marks on her.

    Director:Asaad Kelada
    Writer:Lee Aronsohn

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  11. Who's the Boss? Season 5 Episode 16 - Party Double
    8.0/10(121 votes)

    #11 - Party Double

    S5:E16

    Angela gets invited to a dinner at which Frank Sinatra is to perform; Tony, a huge Sinatra fan, is to be her guest. When business affairs leave her unable to go, Mona goes in her place, but doesn't tell Tony that the ticket is nontransferable.

    Director:Asaad Kelada
    Writer:Danny Kallis

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  12. Who's the Boss? Season 8 Episode 2 - An Affair to Forget
    8.0/10(110 votes)

    #12 - An Affair to Forget

    S8:E2

    After Tony and Angela have confessed their love for each other,they both now want to spend an enchanting evening together.But that isn't that simply,especially since no one can know about it.

    Director:Unknown
    Writer:Gene Braunstein

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  13. Who's the Boss? Season 1 Episode 10 - Requiem
    7.9/10(176 votes)

    #13 - Requiem

    S1:E10

    Tony is moonlighting to raise extra money, which Mona believes is to take care of a secret girlfriend in Brooklyn. Soon the truth comes out: Tony is still paying rent on his recently deceased father's apartment, so that he and Sam will have a place to go just in case things don't work out in Connecticut.

    Director:Asaad Kelada
    Writers:Robert Sternin, Prudence Fraser

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  14. Who's the Boss? Season 2 Episode 1 - It Happened One Summer (1)
    7.9/10(153 votes)

    #14 - It Happened One Summer (1)

    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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  15. Who's the Boss? Season 2 Episode 2 - It Happened One Summer (2)
    7.9/10(156 votes)

    #15 - It Happened One Summer (2)

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

    #16 - Custody (1)

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

    #17 - Custody (2)

    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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  18. Who's the Boss? Season 3 Episode 20 - Older Than Springtime
    7.9/10(124 votes)

    #18 - Older Than Springtime

    S3:E20

    Through Tony's new girlfriend Casey Angela's got a new commercial order for Armando-Fashionwear. But she couldn't think of any spot.Age, too, is a matter because she as the 'experienced' (equals being old) should advertise fashion for the young generation.

    Director:Unknown
    Writer:Unknown

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  19. Who's the Boss? Season 5 Episode 13 - Cardinal Sin
    7.9/10(119 votes)

    #19 - Cardinal Sin

    S5:E13

    Tony goes to an 'Old Timer'-meeting of the Cards in St. Louis,accompanied by Angela. There Tony meets also his old friend Betty.But to prevent approaching attempts he introduces Angela as his wife. When Tony is 'unfaithful', the 'marital row' follows.

    Director:Asaad Kelada
    Writers:Gene Braunstein, Bob Perlow

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  20. Who's the Boss? Season 6 Episode 1 - In Search of Tony
    7.9/10(103 votes)

    #20 - In Search of Tony

    S6:E1

    Holidays on Jamaica. And everyone enjoys the life there.Angela, too, dives right into the holiday-action and has a lot of fun. As it's not Tony, with whom she has that fun, he gets jealous.

    Director:Asaad Kelada
    Writers:Gene Braunstein, Bob Perlow

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  21. Who's the Boss? Season 1 Episode 2 - Briefless Encounter
    7.8/10(222 votes)

    #21 - Briefless Encounter

    S1:E2

    Part of settling into his new home has Tony using Angela's personal bathroom and getting an eyeful when she steps out of the tub. Neither of the two stubborn housemates accept responsibility, and disagree to an extent that Tony's new girlfriend gives him the heave-ho. Mona's advice about role-playing to better understand each other's point of view helps Tony and Angela see that they aren't angry after all.

    Director:Unknown
    Writer:Unknown

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  22. Who's the Boss? Season 1 Episode 11 - Samantha's Growing Up
    7.8/10(163 votes)

    #22 - Samantha's Growing Up

    S1:E11

    Forced to confront the fact that Samantha is not a little girl any more, Tony buys her her first brassiere. When it turns out not to be the kind she wanted, Tony enlists Angela's help in buying Samantha new clothes. He is less than thrilled, however, when Samantha comes home looking a bit too grown up. (Note: This episode was originally titled ""Samantha's First Bra"" but was later changed due to censoring problems.)

    Director:Linda Day
    Writer:Unknown

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  23. Who's the Boss? Season 1 Episode 17 - Eye on Angela
    7.8/10(162 votes)

    #23 - Eye on Angela

    S1:E17

    A local news reporter, Bobbi Barnes, wants to do a story on the daily life of Angela. But when a series of innocent mix-ups leads Tony and Angela to wake up in the same bed, Bobbi's camera crew is waiting in the hall to capture the scene. Bobbi thinks she has a juicy story for her show, but Mona has other ideas.

    Director:Unknown
    Writer:Unknown

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

    #24 - Hunk of the Month

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

    #25 - Thanksgiving at Mrs. Rossini's

    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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Best Episodes Summary

"The Anniversary Show" is the best rated episode of "Who's the Boss?". 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 scored 0.0 points higher than the second highest rated, "Seer of Love".