The WORST episodes of Who's the Boss?

Every episode of Who's the Boss? ever, ranked from worst to best by thousands of votes from fans of the show. The worst episodes of Who's the Boss?!

When Tony Micelli takes a job as housekeeper for Angela Bower, a successful businesswoman, he and his daughter, Samantha, move into Angela's home. Now Tony and Sam must adjust to their new lives with the Bowers- Angela, her son Jonathan, and her mother, Mona.

Last Updated: 6/19/2025Network: ABC (US)Status: Ended
Death and Love (2)
star
4.55
44 votes

#1 - Death and Love (2)

Season 8 - Episode 8 - Aired 11/16/1991

Tony is angry at Angela for her rejection. Meanwhile, she continues to question the sincerity of Tony's intentions.

Directors: Tony Singletary
Misery
star
6.57
46 votes

#2 - Misery

Season 8 - Episode 3 - Aired 10/12/1991

Tony, like it's always his way, overdoes his relationship with Angela. But Angela doesn't dare to tell - and tries to get out of his way.

Directors: Tony Singletary
Writer: Clay Graham
Who's Minding the Kid?
star
6.69
16 votes

#3 - Who's Minding the Kid?

Season 7 - Episode 12 - Aired 12/4/1990

A social worker pays a surprise visit to Tony and Angela in order to check up on Billy. Unfortunately, no one seems to know where he is.

Directors: Tony Singletary
Field of Screams
star
6.75
16 votes

#4 - Field of Screams

Season 8 - Episode 10 - Aired 11/30/1991

Jonathan is looking for a job. A friend of Tony's arranges for Jonathan to work as a ball boy at New York Mets games. A slight mistake during his first game costs him his job -- and the Mets the game.

Tony Bags a Big One
star
6.79
14 votes

#5 - Tony Bags a Big One

Season 8 - Episode 5 - Aired 10/26/1991

While Angela is away on business, Mona begins dating one of her biggest clients. She finds him thoroughly uninteresting and promptly dumps him. In an attempt to prevent from withdrawing his account from the agency, Tony accompanies him on a duck hunt. An accidental gunshot only makes things worse.

Directors: Tony Singletary
Watch Now:Apple TV
Samantha's Growing Up
star
6.81
149 votes

#6 - Samantha's Growing Up

Season 1 - Episode 11 - Aired 1/8/1985

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.)

Directors: Linda Day
Watch Now:Apple TV
Your Grandmother's a Bimbo
star
6.84
19 votes

#7 - Your Grandmother's a Bimbo

Season 5 - Episode 11 - Aired 1/29/1989

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.

Directors: Asaad Kelada
Writer: Bud Wiser
Charmed Lives
star
6.90
79 votes

#8 - Charmed Lives

Season 2 - Episode 26 - Aired 5/13/1986

Angela has found a model to play the part of a princess in a series of pasta commercials. But the client instead chooses a shy photographer, who didn't even want the job.

Writer: Paul Haggis
Who's the Boss?
star
6.92
12 votes

#9 - Who's the Boss?

Season 8 - Episode 14 - Aired 1/25/1992

Angela books up the whole time with some events and visits. Tony has to fall back on excuses to be together with his friends. But Angela catches on to him.

Directors: Tony Singletary
This Sold House
star
6.93
44 votes

#10 - This Sold House

Season 8 - Episode 11 - Aired 12/7/1991

Angela gets a generous offer for her house. Tony persuades her to sell and move into a new one because the current house belongs to 'Angela & Michael' and not to 'Angela & Tony'.

A Well-Kept Housekeeper
star
6.93
44 votes

#11 - A Well-Kept Housekeeper

Season 8 - Episode 6 - Aired 11/2/1991

Tony feels inferior to Angela's success. A letter that addresses him as "Mr. Angela Bower" doesn't help his self-esteem. He takes a second job at a bar, but that proves to be a mistake.

Directors: Tony Singletary
Choose Me
star
6.94
16 votes

#12 - Choose Me

Season 7 - Episode 21 - Aired 3/12/1991

Mona has caught herself another man. But Cliff also falls for Mrs. Rossini who lives at Angela's for some days. Cliff can't decide on one of the both, so a fight for Cliff arises between the two women.

Directors: Tony Singletary
Road Scholar
star
7.00
47 votes

#13 - Road Scholar

Season 6 - Episode 23 - Aired 3/27/1990

Sam has her heart set on attending Tate College, but Tony insists she keep an open mind, so the two take a road trip to visit some schools. Sam eventually gets a letter from Tate requesting an interview, but things don't go as she hoped.

Directors: Asaad Kelada
Mona
star
7.00
48 votes

#14 - Mona

Season 3 - Episode 23 - Aired 5/12/1987

Mona's brother has bought a seedy hotel in New York and used Mona's money for it, too. Because the hotel means a lot for him, Mona goes to New York to help him shape it up again.

Directors: Asaad Kelada
Tony, Can You Spare a Dime?
star
7.02
47 votes

#15 - Tony, Can You Spare a Dime?

Season 8 - Episode 12 - Aired 1/4/1992

Hard times have begun in the advertising industry - and Angela isn't spared either. Tony takes over the financial management because he has economy experiences. He pinches and scrapes wherever he can.When Angela, totally frustrated, goes shopping, she runs into serious troubles with Tony. He without hesitation takes away all her credit cards.

Directors: Tony Singletary
Dinner for Two
star
7.04
100 votes

#16 - Dinner for Two

Season 1 - Episode 6 - Aired 11/20/1984

Tony is greatly anticipating his dinner date with a girl in Brooklyn, just as Angela is preparing for a business dinner for two with a client. When Angela's guest cancels at the last minute, Tony reluctantly stays in Connecticut to keep her company, while attempting to keep, but slightly postpone, his date.

Grandmommie Dearest
star
7.05
42 votes

#17 - Grandmommie Dearest

Season 8 - Episode 9 - Aired 11/23/1991

Mona's mother visits and gives the subtle impression that she doesn't want Tony and Angela to get married. Mona can't convince them that her mother is manipulating them, trying to turn them against each other.

Directors: Tony Singletary
One Flew Over the Empty Nest
star
7.06
18 votes

#18 - One Flew Over the Empty Nest

Season 7 - Episode 5 - Aired 10/16/1990

Sam moves out of the house and into a dorm. Tony's frequent visits make him as popular there as she is, and she begins to feel smothered.

Directors: Tony Singletary
Inherit the Wine
star
7.06
17 votes

#19 - Inherit the Wine

Season 7 - Episode 11 - Aired 11/27/1990

The family fly to Italy to visit Tony's relatives, who have a surprise for him. He is now the owner of a vineyard there.

Directors: Tony Singletary
Cardinal Sin
star
7.06
17 votes

#20 - Cardinal Sin

Season 5 - Episode 13 - Aired 2/7/1989

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.

Directors: Asaad Kelada
Living Dolls
star
7.06
16 votes

#21 - Living Dolls

Season 5 - Episode 19 - Aired 3/28/1989

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.

Directors: John Sgueglia
Writer: Ross Brown
The Hickey
star
7.06
79 votes

#22 - The Hickey

Season 3 - Episode 5 - Aired 11/4/1986

After a party Sam comes home with a love bite and Tony, beside himself, forbids her seeing Todd again. In the evening Sam sneaks out of the house to meet Todd anyway.

Directors: Asaad Kelada
Tony and the Honeymooners
star
7.07
46 votes

#23 - Tony and the Honeymooners

Season 8 - Episode 19 - Aired 2/29/1992

Sam and Hank return from their honeymoon to learn that married couples aren't allowed to stay at the dorm. Tony skeptically agrees to let them stay at the house. Despite a sleepless first night for Tony, he and Hank soon bond. This creates tension between Sam and Hank.

Directors: Tony Singletary
Mrs. Rossini's Uncle
star
7.07
15 votes

#24 - Mrs. Rossini's Uncle

Season 5 - Episode 10 - Aired 1/10/1989

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.

Directors: Asaad Kelada
Writer: Lee Aronsohn
Broadcast Blues
star
7.07
14 votes

#25 - Broadcast Blues

Season 7 - Episode 13 - Aired 12/18/1990

Tony and Sam compete for a college job as a sportscaster. Sam expects Tony to give it his best shot, but she is afraid that, since she is running against him, he will let her win. Tony's audition video, however, misleads Sam about his intentions.

Directors: Tony Singletary