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The Best Episodes of Who's the Boss? Season 5

Every episode of Who's the Boss? Season 5 ranked from best to worst. Discover the Best Episodes of Who's the Boss? Season 5!

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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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  1. #1 Fan Favorite
    Who's the Boss? Season 5 Episode 1 - Sam's Car
    7.3/10(101 votes)

    #1 - Sam's Car

    S5:E1

    Young Samantha has reached a teenage milestone - she has her driver's license! But in upscale Connecticut she feels left out when Bonnie gets a brand new car but Tony buys Samantha a hazard light on wheels! It comes down to pride vs love when it's discovered she's parking blocks away from her school.

    Director:Asaad Kelada
    Writers:Bob Perlow, Gene Braunstein

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  2. Who's the Boss? Season 5 Episode 2 - My Fair Tony
    7.4/10(91 votes)

    #2 - My Fair Tony

    S5:E2

    In an effort to better himself, Tony heads off to college. The public speaking class is headed up by a strict grammer enthusiast who singles Tony out as an impossible case. Its My Fair Lady as Tony does a complete turnaround, but he alienates himself from his family and friends and must rely on the ""inner Tony"" to figure out who he really wants to be.

    Director:Asaad Kelada
    Writer:Unknown

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  3. Who's the Boss? Season 5 Episode 3 - Nineteen Again
    7.2/10(94 votes)

    #3 - Nineteen Again

    S5:E3

    Tony has been invited to a frat party and Angela accompanies him. But there Angela drinks a little too much of the (with alcohol mixed) bowle and 'entertains' those present. In the end Angela and Tony land up in the campus jail.

    Director:Asaad Kelada
    Writer:Clay Graham

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  4. Who's the Boss? Season 5 Episode 4 - Yankee Doodle Micelli
    7.8/10(95 votes)

    #4 - Yankee Doodle Micelli

    S5:E4

    Tony feels guilty when he remembers he got his grandfather in trouble when he was a child, causing him to never take the American citizen swearing in, so Tony does the swearing in for his grandfather.

    Director:Asaad Kelada
    Writer:Unknown

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  5. Who's the Boss? Season 5 Episode 5 - A Jack Story
    7.2/10(88 votes)

    #5 - A Jack Story

    S5:E5

    Angela engages a new employee. Because in the evening the both work together more and more often and longer, Tony fears the worst:he gets jealous.

    Director:Asaad Kelada
    Writer:Unknown

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  6. Who's the Boss? Season 5 Episode 6 - Double Dump
    7.3/10(90 votes)

    #6 - Double Dump

    S5:E6

    Samantha and Mona both break up with their boyfriends on the same night, so they go out to eat at a restaurant to clear their minds, which troubles Tony.

    Director:Asaad Kelada
    Writer:Eric Gilliland

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  7. Who's the Boss? Season 5 Episode 7 - Life With Father
    6.9/10(80 votes)

    #7 - Life With Father

    S5:E7

    Samantha wants to go to Vermont ski lodge for the weekend, but Tony forbids her. Sam goes anyway. Along the way, she remembers everything her father did, even the embarassing moments!!

    Director:Asaad Kelada
    Writer:Danny Kallis

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  8. Who's the Boss? Season 5 Episode 8 - A Spirited Christmas
    7.0/10(90 votes)

    #8 - A Spirited Christmas

    S5:E8

    The wife of Mona's brother has died. But to go to heaven she must make Mona reconcile with her brother. Tony is picked out as the mediator.

    Director:Asaad Kelada
    Writer:Unknown

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  9. Who's the Boss? Season 5 Episode 9 - Teacher's Pet
    6.9/10(93 votes)

    #9 - Teacher's Pet

    S5:E9

    Mason should run a seminar at the college, which also Tony attends. Because Mason is quite nervous Tony and Angela give him some hints: among these is also the tip that he should concentrate on one person. And Mason has choosen this one person: Tony.

    Director:Asaad Kelada
    Writer:Clay Graham

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  10. Who's the Boss? Season 5 Episode 10 - Mrs. Rossini's Uncle
    6.8/10(87 votes)

    #10 - Mrs. Rossini's Uncle

    S5:E10

    Mrs. Rossini visits Tony. Accompanying her is her young uncle Al.Al is attending the nearby Beauty College and Tony should take care of him. In the course of this Sam and Al come closer.

    Director:Asaad Kelada
    Writer:Lee Aronsohn

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  11. Who's the Boss? Season 5 Episode 11 - Your Grandmother's a Bimbo
    6.8/10(97 votes)

    #11 - Your Grandmother's a Bimbo

    S5:E11

    Mona has saved the order for Angela and designs now the new get-up for the magazine 'Mature Woman'. Jonathan runs for treasurer in his school. For the magazine's cover Mona let herself photograph scantily dressed. When Jonathan schoolfellows see this cover, his chances getting elected seem to be gone.

    Director:Asaad Kelada
    Writer:Unknown

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  12. Who's the Boss? Season 5 Episode 12 - Ton-An-Enterprises
    7.1/10(82 votes)

    #12 - Ton-An-Enterprises

    S5:E12

    Again Sam comes home with an expensive T-shirt. This time Tony wants to show her that she can have them cheaper and produces some of them himself. Angela and Sam persuade him selling them at the flea market. Both of them help him, especially Sam hopes she can get rid of her debts which she has made at Jonathan. But it happens what has to happen: Angela and Tony quarrel.

    Director:Unknown
    Writer:Clay Graham

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  13. Who's the Boss? Season 5 Episode 13 - Cardinal Sin
    7.9/10(103 votes)

    #13 - 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:Bob Perlow, Gene Braunstein

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  14. Who's the Boss? Season 5 Episode 14 - Winter Break
    7.4/10(91 votes)

    #14 - Winter Break

    S5:E14

    Tony and Sam spend a weekend together skiing in Vermont. There Tony meets Lisa, his skiing instructor. But Sam isn't happy about her father's fling. Inbetween - at home - Angela and Mona catches a cold.

    Director:Asaad Kelada
    Writer:Unknown

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  15. Who's the Boss? Season 5 Episode 15 - First Date
    7.8/10(91 votes)

    #15 - First Date

    S5:E15

    Discouraged that Angela had to pay for an escort for a dinner event, Mona convinces Tony to ask her out on a date. The date hardly seems like a first for them, though, as they discover how much they know about each other. Things get ugly when Angela learns the reason behind the evening, and attacks an obnoxious comedian.

    Director:Asaad Kelada
    Writer:Daniel Palladino

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  16. Who's the Boss? Season 5 Episode 16 - Party Double
    8.1/10(105 votes)

    #16 - 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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  17. Who's the Boss? Season 5 Episode 17 - Boozin' Buddies
    7.3/10(88 votes)

    #17 - Boozin' Buddies

    S5:E17

    Samantha gets drunk one night, and when she sees Tony drinking the next day, she calls him a hypocrite because he told her drinking was wrong.

    Director:Asaad Kelada
    Writer:Unknown

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  18. Who's the Boss? Season 5 Episode 18 - Heather Can Wait
    7.6/10(89 votes)

    #18 - Heather Can Wait

    S5:E18

    The Bowers get new neighbors: the Harpers. But they are a little bit too snooty and an big argument between Tony/Angela and the Harpers comes up. But Jonathan and Heather, the Harper's daughter, have fallen for each other.

    Director:Asaad Kelada
    Writer:Unknown

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  19. Who's the Boss? Season 5 Episode 19 - Living Dolls
    6.7/10(110 votes)

    #19 - Living Dolls

    S5:E19

    Sam visits a beauty school run by Angela's friend. While there, she meets Charlie, a friend of hers from the old neighborhood, who is living there. Charlie is unhappy with her life there, and is considering running away.

    Director:Unknown
    Writer:Unknown

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  20. Who's the Boss? Season 5 Episode 20 - Men are People, Too
    6.8/10(85 votes)

    #20 - Men are People, Too

    S5:E20

    Angela hires a shy contractor to put a skylight in the kitchen. He takes an immediate liking to Mona, who agrees to go out with him. When he learns that he is not the only man in Mona's life, he abandons the skylight job. Tony accuses Mona of having no respect for men's feelings.

    Director:Asaad Kelada
    Writer:Eric Gilliland

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  21. Who's the Boss? Season 5 Episode 21 - Working Girls
    7.7/10(88 votes)

    #21 - Working Girls

    S5:E21

    At a practical program, where students are assigned different jobs, for Sam and Bonnie there are only two left: domestic engineer with Tony or advertising with Angela. Sam decides in favor of the housekeeping job which she regrets soon. The following day Bonnie and Sam switch their jobs but working for Angela isn't any fun, neither.

    Director:Frank Bonner
    Writer:Jake Weinberger

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  22. Who's the Boss? Season 5 Episode 22 - Tony Does Golf
    7.3/10(88 votes)

    #22 - Tony Does Golf

    S5:E22

    Tony has a new passion: golfing. Angela wins a country club membership for Tony. There Tony meets the owner of the biggest nationwide sport articles store who currently gives away a big advertising order. And of course, Angela's after this order, too.

    Director:Asaad Kelada
    Writers:Bob Perlow, Gene Braunstein

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  23. Who's the Boss? Season 5 Episode 23 - Ode to Angela
    7.5/10(92 votes)

    #23 - Ode to Angela

    S5:E23

    Angela married Brian 20 years ago. As this was just meant as a college joke, Brian drove down to Mexico the following day to annul this marriage. But now when Brian wanted to marry again, he is told, that his marriage with Angela is still valid.

    Director:Asaad Kelada
    Writer:Daniel Palladino

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  24. Who's the Boss? Season 5 Episode 24 - In Sam We Trust
    7.4/10(84 votes)

    #24 - In Sam We Trust

    S5:E24

    Sam's friend Scott gets nervous about French finals, so on test day, Sam gives Scott the answers. When Tony finds out, he takes Sam's car privileges. But when Sam has to take chemistry finals, someone gives Sam the answers to the test, but she does not use it. When the teacher sees the answers under Sam's desk, he calls Tony. But will anyone believe anything she says?

    Director:Asaad Kelada
    Writer:Unknown

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  25. Who's the Boss? Season 5 Episode 25 - It's Somebody's Birthday
    7.7/10(82 votes)

    #25 - It's Somebody's Birthday

    S5:E25

    Tony gets a new car as birthday present. First his pride forbids to accept it but after some encouragement he, however, decides to keep the car. But selling his Van brings up memories of good old times.

    Director:Asaad Kelada
    Writer:Unknown

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Season 5 Ratings Summary

"Sam's Car" is the best rated episode of "Who's the Boss?" season 5. It scored 7.3/10 based on 101 votes. Directed by Asaad Kelada and written by Bob Perlow, Gene Braunstein, it aired on 10/18/1988. This episode is rated 0.1 points higher than the second-best, "My Fair Tony".