If there's one thing that sitcom fans love, it's when characters get married and/or have babies. But those relationships don't always work out, or even make sense. In the case of Night Court, a sitcom classic that doesn't seem to be streaming anywhere, a surprising number of those relationships centered around Judge Harold T. Stone. But everyone got mixed up in their fair share of romantic entanglements, some good and several bad.
WORST: Harry Stone And Margaret Turner
Early in season eight, Harry met a court reporter named Margaret Turner. She was a largely uninterested in him, so Harry went to Dan for advice. Naturally, that was a bad idea. But their relationship did lead to them dating and then eventually being engaged. That didn't last long, though, and the duo split up in season nine. It wasn't an especially interesting relationship, and added little to the show.
BEST: Harry Stone And Billie Young
The first few seasons of Night Court were a revolving door of new cast members and characters, particularly in the public defender role. One of the several characters in that position was Billie Young, who was only there for season two before leaving the series.
Of all the characters Harry had relationships with, Billie might have been the most interesting. It would have been great to see that play out.
WORST: Bob And June Wheeler
A lot of sob stories came through Judge Stone's courtroom but none were more sad than the Wheelers. The duo were constantly in the cartoonishly worst situations, which included having their hot dog cart stolen by a tornado. The Wheelers were fan favorites, and should be, but one can't help but wonder how much of their misfortunes would have been solved by going their separate ways.
BEST: Dan Fielding And Sheila
Assistant district attorney Dan Fielding was a sleazy, lecherous man who wanted money, power and women. Knowing him, he only wanted the money and power because he hoped women would follow. The one woman absolutely who owned him was Sheila, a notorious maneater who was more sexually aggressive than Dan.
His repeated attempts to go out with her constantly fell apart, leading to some of the funniest moments on the show. It was one of the few times that Dan was on the defensive with a woman he was interested in.
WORST: Harry Stone And Lana Wagner
During season one of the series, the court clerk was a woman named Lana Wagner. She was a tough, no-nonsense type person who ran the courtroom well. A relationship between her and the new, young judge was built up rather quickly but went nowhere. She was gone by season two and replaced by Mac Robinson. That was for the best as Harry and Lana had little on screen chemistry.
BEST: Nostradamus 'Bull' Shannon And Joy Buscaglia
Bull, the towering bailiff of the Judge Stone's courtroom, was a powerful and well meaning dullard who misunderstood virtually everything. Joy was briefly Harry's personal assistant, a blind woman whose sharp wit and abrasive attitude made her difficult for the staff to deal with.
She struck an immediate connection with Bull, which was as adorable as it was frightening.
WORST: Christine Sullivan and Tony Giuliano
Christine met Tony, an NYPD detective, just before he was supposed to leave New York to work with the DEA. Their intense mutual attraction to each other led them to get married after only knowing each other for a very short time. They divorced not long after that, though Christine found she was pregnant with his child. Their relationship fizzled quickly and faded from the series, which was the best case scenario.
BEST: Harry Stone And Christine Sullivan
After the introduction of Christine Sullivan, a competition for her affections began between Harry and Dan. Even when each one of the three of them was interested in someone else, fans knew one of those two pairs would eventually come to fruition. Unfortunately, that never happened as the series was cancelled in season nine just as the Harry/Christine relationship was starting to heat up a bit.
30 Rock paid homage to this when Kenneth and Tracy teamed up to film a satisfying ending to Night Court that featured Harry and Christine getting married. Finally.
WORST: Dan Fielding And Christine Sullivan
It's entirely possible that Dan is one hundred percent incapable of having a healthy relationship with a woman. If it was possible with any woman, that woman might have been Christine. He pursued her relentlessly for years, coming close to sleeping with her on a number of occasions. But he eventually realized he respected her too much and didn't sleep with her when he had the chance. That epiphany did not stop him from continuing to act like a real horndog in court, though.
BEST: Mac Robinson And Quon Le Robinson
There is an argument to be made that this was the best relationship on Night Court. It's definitely the most healthy one. A Vietnam Veteran, Mac helped Quon Le's family during the war. When she came to America several years later, she sought Mac out. He married her to allow her to stay the country, but grew to love her the same way she loved him. The Mac and Quon Le relationship was, by far, the most stable one on the series.