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Who's the Boss? (1984 – 1992)

1984 • 8 seasons • Comedy • TV-PG
On September 29, 2026
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All seasons

Who's the Boss? — Season 5

25 episodes · Oct 18, 1988

1. Sam's Car
Oct 18, 1988 · 23m

Samantha had finally earned her driver’s license, a rite of passage for any teenager. Yet in their affluent Connecticut neighborhood, a sense of exclusion began to creep in. Bonnie arrived with a gleaming new car, while Samantha received a …

2. My Fair Tony
Oct 25, 1988 · 23m

Driven by a desire for personal growth, Tony leaves home to attend college. His public speaking class is led by an exacting instructor with a passion for grammar, who quickly identifies Tony as a particularly challenging student. The experi…

3. Nineteen Again
Nov 1, 1988 · 23m

Tony received an invitation to a fraternity gathering, and Angela insisted on going with him. However, Angela indulged a bit too freely in the punch—a concoction laced with alcohol—and found herself amusing the crowd with unexpected antics.…

4. Yankee Doodle Micelli
Nov 22, 1988 · 23m

A pang of guilt would strike Tony whenever he recalled a childhood misstep that had inadvertently caused difficulty for his grandfather, preventing him from ever formally taking the oath of citizenship. Consequently, it fell to Tony to perf…

5. A Jack Story
Nov 29, 1988 · 23m

Angela has taken on a new colleague, and as they find themselves working late into the evenings with increasing frequency and duration, Tony’s anxieties grow – he is consumed by jealousy.

6. Double Dump
Dec 6, 1988 · 23m

It happened that Samantha and Mona ended things with their respective boyfriends on the very same evening, prompting them to seek solace in a dinner at a restaurant—a development that caused Tony considerable unease.

7. Life With Father
Dec 13, 1988 · 23m

Samantha longed to escape to a Vermont ski lodge for the weekend, yet Tony had expressly denied her request. Undeterred, she went regardless. As she traveled, memories flooded back – every action of her father surfaced, encompassing even th…

8. A Spirited Christmas
Dec 20, 1988 · 23m

Mona’s brother’s wife has passed away. However, her passage to heaven hinges on Mona and her brother finding reconciliation. It falls to Tony to act as their intermediary.

9. Teacher's Pet
Jan 3, 1989 · 23m

Mason was scheduled to lead a seminar at the college, an event Tony himself would be attending. Sensing his apprehension, both Tony and Angela offered encouragement, suggesting he focus his attention on a single individual within the group.…

10. Mrs. Rossini's Uncle
Jan 10, 1989 · 23m

Mrs. Rossini came to see Tony, bringing with her a younger relative, her uncle Al. Al was studying at the local beauty school, and Mrs. Rossini asked Tony to keep an eye on him. As time passed, a connection began to develop between Sam and …

11. Your Grandmother's a Bimbo
Jan 29, 1989 · 23m · 1.0

Mona has secured an order for Angela and is now designing the new look for 'Mature Woman' magazine. Meanwhile, Jonathan is campaigning for treasurer at his school. For the magazine’s cover, Mona agreed to be photographed in a revealing styl…

12. Ton-An-Enterprises
Jan 31, 1989 · 23m

Once again, Sam returned home with a costly T-shirt. This time, Tony felt compelled to demonstrate that he could obtain similar items for less, even going so far as to produce some himself. Angela and Sam encouraged him to sell them at the …

13. Cardinal Sin
Feb 7, 1989 · 23m · 1.0

Tony attended a gathering of longtime fans of the Cardinals baseball team in St. Louis, bringing Angela with him. It was there he unexpectedly encountered an old friend, Betty. To discourage any unwanted attention, Tony introduced Angela as…

14. Winter Break
Feb 14, 1989 · 23m

Tony and Sam escaped for a weekend of skiing in Vermont. It was there that Tony met Lisa, his assigned ski instructor. However, Sam found himself troubled by the casual relationship Lisa’s father seemed to be involved in. Meanwhile, back at…

15. First Date
Feb 21, 1989 · 23m

Mona, disheartened by the necessity of Angela footing the bill for an escort at a dinner engagement, persuaded Tony to ask her out instead. Yet, their date felt remarkably familiar from the start; they quickly realized how much they already…

16. Party Double
Feb 28, 1989 · 23m

Angela received an invitation to a dinner featuring a performance by Frank Sinatra, and she was to bring Tony, who adored him. Unfortunately, pressing business obligations prevented her from attending, so Mona stepped in as her substitute. …

17. Boozin' Buddies
Mar 7, 1989 · 23m

The following night found Samantha unsteady with drink, and the sight of Tony enjoying a beverage the next morning sparked a sharp accusation. She confronted him, calling him a hypocrite for having contradicted his earlier pronouncements ag…

18. Heather Can Wait
Mar 21, 1989 · 23m

The Bowers welcomed new neighbors – the Harpers. However, the Harpers possessed a certain aloofness that quickly proved unsettling, culminating in a rather heated disagreement between Tony and Angela Bowers and their new arrivals. Complicat…

19. Living Dolls
Mar 28, 1989 · 23m

While exploring a cosmetology school—a favor for Angela—Sam encountered Charlie, an acquaintance from their childhood, who was also residing at the institution. A palpable unhappiness clung to Charlie; she spoke of discontentment and confes…

20. Men are People, Too
Apr 4, 1989 · 23m

Angela engaged a quiet contractor to install a skylight in her kitchen. He quickly developed an affection for Mona and, surprisingly, she agreed to accompany him on a date. Discovering that he wasn’t the only man vying for her attention, ho…

21. Working Girls
Apr 11, 1989 · 23m

In a hands-on program where students were given varied responsibilities, only two options remained for Sam and Bonnie: assisting Tony with household tasks or joining Angela’s advertising team. Sam chose the domestic role, a decision she qui…

22. Tony Does Golf
Apr 25, 1989 · 23m

Tony had recently taken up golf with considerable enthusiasm. Angela, recognizing his burgeoning interest, secured him a membership at the local country club. It was there that Tony encountered the proprietor of a vast national sporting goo…

23. Ode to Angela
May 2, 1989 · 23m

Twenty years ago, Angela and Brian entered into a marriage—a whimsical arrangement initially conceived as a college jest. The next day, Brian traveled to Mexico to have the union formally annulled. However, when he later sought to remarry, …

24. In Sam We Trust
May 9, 1989 · 23m

Scott was beside himself with anxiety about his French final exams, and on the day of the test, Sam, wanting to help, slipped him the answers. The news reached Tony, who responded by taking away Sam’s driving privileges. Later, when Sam fac…

25. It's Somebody's Birthday
May 16, 1989 · 23m

For his birthday, Tony received a new car—a generous gift that initially sparked resistance within him. Pride made him hesitant to accept such an extravagance, yet with gentle persuasion, he ultimately decided to keep it. Still, parting wit…