Take this boss trivia quiz on “Who’s the Boss?”

By: Julie Medina
Image: Youtube

About This Quiz

Who’s the Boss was all about making us laugh while poking fun at traditional gender roles. Relive the 80s and the antics of Tony, Angela, Mona, Sam and Johnathan with this boss trivia quiz.

What did Tony do before he became a live-in housekeeper?

Tony Micelli is a former second baseman for the St. Louis Cardinals who was forced to retire due to a shoulder injury. He did well as a TV father. The character "Tony Micelli" was ranked #23 in TV Guide's list of the "50 Greatest TV Dads of All Time" (20 June 2004 issue).

Why did Tony decide to become a live-in housekeeper?

An interesting coincidence, besides playing a Tony in both roles, before "Who's the Boss", Tony Danza starred in the series, "Taxi", whose theme song was titled Angela. In "Who's the Boss", his character works for a character named Angela.

What is the name of Tony’s daughter?

Sam (Samantha) has Tony’s street smarts and gets into fights easily. She is one in a million, well, at least one in 1500. There were 1500 girls who auditioned for the role of Samantha Micelli.

Who had a big hand in hiring Tony?

When Angela confronts Mona, she counters, “Oh, don't be sexist. A man can do meaningless, unproductive work just as well as a woman.” Mona was originally intended to be Angela's older sister, but producers were unable to find an age appropriate actress they liked for the part. As a result, they decided to redevelop Mona to be Angela's mother instead.

How did Who’s the Boss break norms?

The breaking of norms allowed the sitcoms to examine issues that weren’t discussed as often. The pilot episode was filmed in October 1983 but held back from ABC executives for nearly a year due to the producers of the series being afraid that the show would be rejected by ABC executives if pitched as a mid-season replacement series.

What does Angela do for a living?

Angela was an Advertising Executive. It's interesting that in real life Judith Light is was not a "traditional" woman as she decided not to have any children. Although they both play family matriarchs, neither Judith Light nor Katherine Helmond have any children in real life.

What is the name of Angela’s son?

Jonathan Bower, portrayed by Danny Pintauro, needed a father figure which he found with Tony. It's interesting to note that both Judith Light and Danny Pintauro are the only child in their family.

What was the name of Angela’s ex-husband?

Michael Bower, was portrayed by James Naughton. He is a very accomplished actor. He won his first Tony Award for Best Actor in a Musical in 1990 for City of Angels. In 1997 he won a second Tony Award with his portrayal of lawyer Billy Flynn in the musical Chicago. He played the role of Willy Brandt in Democracy on its U.S. première in 2004. His films include The Paper Chase and The First Wives Club. In 2006, he appeared in the movie The Devil Wears Prada, opposite Meryl Streep. In 2006, he played Fuzzy Sedgwick in Factory Girl.

Although Angela starts out as an Advertising Executive what does she eventually do?

In season three, Angela strikes out on her own, opening up her own agency. It sure beats how Judith Light started on the ABC daytime soap opera One Life to Live where she played the role of Karen Wolek, who becomes an alcoholic prostitute after she becomes bored with her life as a housewife. Although for that role, she won two Daytime Emmy Awards for Outstanding Lead Actress in a Drama Series.

When Tony and Sam move from Brooklyn, what longtime friend did they leave behind?

Mrs. Rossini, was portrayed by Rhoda Gemignani. Although Tony and Sam left Brooklyn, Mrs. Rossini comes to see them occasionally. She is no stranger to TV, she also played in other sitcoms, including The Bob Newhart Show, The Jeffersons, Just Shoot Me! as Elliot's mother, The Twilight Zone, Family Album (as Ruby DeMattis), Friends, Seinfeld, Full House, Kojak, The Mary Tyler Moore Show, NBC Special Treat, Walker, Texas Ranger and many others.

Although Tony continues to be a live-in housekeeper, what else does he eventually do?

Tony decides to go back to college to become a teacher. Off camera during the series, Tony Danza was the pitcher for the sitcom's softball team, even though his character, Tony Micelli, was a retired second baseman for the St. Louis Cardinals. Milano’s father was the team's first baseman.

During the eight seasons, TV viewers watched Jonathan grow up. Where does his schooling leave off at the end of the series?

Jonathan was still in high school when the series ended. In real life, after the conclusion of that series, he was less frequently cast. Pintauro went on to act in stage productions like The Velocity of Gary and Mommie Queerest. He also worked as a Tupperware sales representative and, as of 2013, was managing a restaurant in Las Vegas.

What is the name of Sam’s best friend?

Samantha's best friend is Bonnie (Shana Lane-Block) and is a recurring character. She is known for her work on Days of Our Lives (1965), Who's the Boss? (1984) and Blackout (1985).

What was the name of Samantha’s boyfriend?

Romance comes into her Samantha’s life in the form of boyfriend Jesse Nash (played by Scott Bloom) during her senior year of high school and into college. We hope that the having a "boyfriend" helped her be happy with the show. Since after the show's seventh season, Alyssa Milano tried to break out of her contract to pursue an academic career, but her proposal was refused.

Do you remember the name of Tony’s father-in-law?

Nick Milano was portrayed by actor James Coco. When James died of a heart attack in real life, his character was written out as having died as well in the show. Thus enabling the writers to provide a funeral episode and tribute.

Angela has a steady romantic interest in the series, what is his name?

Geoffrey Wells played Angela’s romantic interest. The actor, Robin Thomas could make Tony’s character jealous at times. In real life Judith Light is still married to the same man, not like her character who was a divorcée. She has been married to television actor Robert Desiderio since 1985, when they met while co-starring on One Life to Live.

Tony has a variety of girlfriends who come and go, what was the name of the reoccurring character in seasons six and seven?

Kathleen Sawyer was portrayed by Kate Vernon in seasons six and seven. In 1990 Vernon portrayed Kathleen Sawyer in a four-episode arc on Who's the Boss?, followed by extended appearances on L.A. Law in 1994 as A.D.A. Belinda Fox and on Nash Bridges in 1996-97 as Whitney Thomas. More recently, Vernon portrayed the recurring role of Ellen Tigh on Battlestar Galactica. In 2010 she guest starred in two episodes of Heroes as Vanessa Wheeler, and in 2014 portrayed Diana Sydney on The 100.

What character did Mathew Perry (pre-‘Friends”) play in Who’s the Boss?

Mathew Perry, was portrayed Benjamin Dawson. When Sam moved out of the noisy dorm she moved in with a college-aged couple, Benjamin and Beth. Mathew Perry is know for his "Friends" Fame and now stars in the remake of the "Odd Couple".

There were some famous guest stars that appeared on the show. Which one of these actors were on the show?

Frank Sinatra make a guest appearance in a 1989 episode. Ray Charles starred in 1987. And Mike Tyson guest starred in 1990.

Johnathan is talking to a very well-known guest star, who is it? “Hi there. Who are you?”Jonathan: “I'm my mother's son.” “What a coincidence—so am I.”

Ray Charles couldn’t see the resemblance between mother and son and had a smart reply to Jonathan’s answer. Speaking of the famous guest stars, Danza asked Frank’s daughter, Tina, her father would make a guest appearance on the then very popular show. Danza’s mother didn’t believe her son was a real star until he introduced her to the singer.

Who is Angela speaking to? “That was beautiful, but I'm afraid we won't be able to use the song.” “Oh, honey, I can do it better!”

In the episode, Samantha's boyfriend Chad writes a song just for her. Word gets around, and the tune is heard by legend Ray Charles whom Angela coerces into recording it for her ad agency. When Chad starts seeing another girl, Samantha demands the recording not take place and refuses to speak to Angela unless the song is dumped. It takes a stellar performance of the song by Ray to make Samantha change her mind.

What happens in the episode, “Seer of Love” ?

Tony and Angela were supposed to get married halfway through the show. However, the producers changed their minds, worried that Tony and Angela’s marriage would ruin the show for syndication; they believed that new viewers finding the show would watch more if the sexual tension was ongoing.

In what episode does Tony play an easygoing guy who looks just like himself.

Angela escapes a tense Tony by going to a resort where she meets a man who seems to be his easygoing twin (Tony Danza in a dual role). She likes the relaxed Tony so much better which gets her thinking. The series ended with Tony and Angela breaking up but with Tony appearing on Angela's doorstep to apply for the housekeeper job in a scene that is almost identical to the opening scene in the pilot episode.

In the episode, A Well-Kept Housekeeper, Tony can't resist bidding for a painting he can't afford to impress the country club members. To pay for it, he takes a job as a shirtless waiter. Then what happens?

Sam awkwardly discovers her Dad took on a second job, to her and his embarrassment. It wasn't just the shirtless Tony that kept people viewing. It was the dynamic between Tony and Angela. Although Judith Light wasn't sure she wanted to be on a sitcom but she followed the script’s instruction and walked across the stage wearing only a robe. Sensing Danza was looking at her butt, she asked the unscripted question, “What are you looking at?” Danza laughed. Danza claimed he knew immediately that she was going to get the part.

What was the name of the show’s theme song?

The show's theme song, "Brand New Life", was written by series creators and executive producers Cohan and Hunter, with music composed by Larry Carlton and Robert Kraft. It was all about the brand new life Tony and Sam would have in Connecticut.

Which of these choices are the correct words to the theme song?

We hope you’re singing it too, because it’s all of the above. Here are all the words: There's a time for love and a time for living. You take a chance and face the wind. An open road and a road that's hidden. A brand new life around the bend. There were times when I lost a dream or two.Found the trail, and at the end was you. There's a path you take and a path not taken, the choice is up to you, my friend. Nights are long but you might awake to a brand new life, brand new life, brand new life around the bend.

In the episode, “Tony Does Golf” how does Tony get a membership to the country club?

Angela wins a free membership in the country club raffles and gives the membership to Tony. Unfortunately, Tony gets snubbed by the other members until he meets a self-made millionaire, Lowell Michaels. When the ladies here about such a potential client, just what Angela's agency needs to recover, Mona emotionally blackmails Tony to abuse his new friend's confidence to arrange a business appointment.

We all know the van that Tony drives, what does Angela drive?

While Angela drove a Jaguar, Tony was content driving his beat-up blue van. It was another way that the writers could show nontraditional roles, with the macho man not needing a hot car to prove his masculinity.

What was Tony’s catch phrase?

In reality, Tony is not as calm and well-mannered as he was on the show. Danza was sentenced to 250 hours of community service after a fight with a bouncer at a New York hotel. He was facing jail time, but his lawyer argued that it would disrupt production of his upcoming show.

In the episode, Frankie and Tony Are Lovers, Tony gets auctioned off to help Mrs. Rossini at the fair. Who buys him?

Frankie, an old flame of Tony “bought” Tony, which made Angela jealous. So jealous she realized how she really feels about Tony. This sparked many other episodes when they realize they love each other, but neither one can admit to it. And then of course, the preparation for the marriage episodes.

During which years did Who’s the Boss air?

Who’s the Boss aired for eight seasons, from 1984 to 1992. They were redefining traditional roles and remained relevant all eight seasons .In its eighth season, the network moved the show to Saturday night, where the ratings plummeted low enough that it was cancelled.

How many nominations did Who's the Boss receive?

Who’s the Boss was nominated for more than forty awards. The show was so popular, there were two short-lived spin-offs from it. "Charmed Live"s lasted three episodes, and was based on spokesmodels-turned-roommates Fran Drescher and Donna Dixon’s characters from the season two finale, “Charmed Lives." "Living Dolls", was about a group of young models living together. It ran for 12 episodes in 1989. It starred Leah Remini as Charlie Briscoe, Samantha’s friend, but it’s mostly known as Halle Berry’s acting debut.

How many awards did the series win?

Even though it had over 40 nominations it only won two awards, one Emmy and one Golden Globe. For the Golden Globe Katherine Helmond (Mona) won for Best Performance by an Actress in a Supporting Role in a Series, Miniseries or Motion Picture Made for Television. The series also won an Emmy Award for Outstanding Lighting Direction (Electronic) for a Comedy Series, Mark J. Levin (lighting director) for the episode "A Spirited Christmas".

Melissa Milano was frequently nominated at the annual Young Artist Awards, how many awards did she win?

Melissa Milano earned three awards at the annual Young Artist Awards for her portrayal of Samantha. But she wasn't the only one, Danny Pintauro and recurring guest Scott Bloom received one award each.

Several versions of Who's the Boss have been produced for foreign television markets. Which of these markets?

​There are many more countries than you can imagine showing the series including Argentina, Spain, Russian, Polish and Turkey. In many cases the names of the lead characters were changed, some are dubbed and others are remakes.

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