As of July 2026, Who's the Boss? Season 5 aired in 1988 with 25 episodes — streaming now on Amazon Prime Video. Full episode guide and where to watch below.
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Who's the Boss? Season 5

1988 25 Episodes Comedy ⭐ 7/10

Who's the Boss? Season 5 has quietly become one of the more dependable comedies currently available on and . A single, tightly-focused season means there is plenty to get through without ever feeling padded. 302 viewers have already rated it on TMDB — the kind of consensus that does not happen by accident. Tony Danza sets the tone, and the rest of the cast matches it scene for scene. Put it on tonight and see for yourself.

Who's the Boss? Season 5 arrived without much fanfare and built its audience the hard way — through word of mouth. The jokes in Who's the Boss? Season 5 land because the characters underneath them are worth caring about. Season 5 of Who's the Boss? Includes 25 episodes. It aired from October 1988 to May 1989. Tony Danza and Judith Light lead a cast that brings real weight to the material. It was aired in 1988. The timing in Who's the Boss? Season 5 is precise enough that even the throwaway lines land on a second watch. There is real craft here, even in the moments that do not fully land.

For viewers who want something light without wanting something stupid, Who's the Boss? Season 5 respects your intelligence. It has built its own audience without needing a direct comparison. It is a manageable watch, easy to fit into a single week. Tony Danza sets the tone, but the supporting cast is where a lot of the best moments come from. A reliable pick for any night you want quality comedy without the homework.

📡 Where to Watch Who's the Boss? Season 5

🇺🇸 United States
🇨🇦 Canada
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🎬 Who's the Boss? Season 5 — Episode Guide

E1
Sam's Car
1988-10-18
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 scho...
E2
My Fair Tony
1988-10-25
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 th...
E3
Nineteen Again
1988-11-01
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.
E4
Yankee Doodle Micelli
1988-11-22
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.
E5
A Jack Story
1988-11-29
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.
E6
Double Dump
1988-12-06
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.
E7
Life With Father
1988-12-13
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!!
E8
A Spirited Christmas
1988-12-20
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.
E9
Teacher's Pet
1989-01-03
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.
E10
Mrs. Rossini's Uncle
1989-01-10
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.
E11
Your Grandmother's a Bimbo
1989-01-29
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 gon...
E12
Ton-An-Enterprises
1989-01-31
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 ...
E13
Cardinal Sin
1989-02-07
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.
E14
Winter Break
1989-02-14
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.
E15
First Date
1989-02-21
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 ...
E16
Party Double
1989-02-28
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.
E17
Boozin' Buddies
1989-03-07
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.
E18
Heather Can Wait
1989-03-21
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.
E19
Living Dolls
1989-03-28
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.
E20
Men are People, Too
1989-04-04
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.

🎭 Cast of Who's the Boss? Season 5

Tony Danza
Tony Danza
Tony Micelli
Judith Light
Judith Light
Angela Bower
Alyssa Milano
Alyssa Milano
Samantha Micelli
Danny Pintauro
Danny Pintauro
Jonathan Bower
Katherine Helmond
Katherine Helmond
Mona Robinson

📋 All Seasons of Who's the Boss?

Season 1Season 2Season 3Season 4Season 6Season 7Season 8

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