The BEST episodes of Caroline in the City
Every episode of Caroline in the City ever, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Caroline in the City!
A situation comedy centered on Caroline Duffy, a young cartoonist living in the Tribeca neighborhood of New York City. Each episode begins with a brief animated sequence reflecting the autobiographical nature of her syndicated newspaper cartoon strip Caroline in the City, explicitly compared with the real comic strip Cathy in several episodes.
#1 - Caroline and the Condom
Season 1 - Episode 24 - Aired 8/5/1996
Caroline's writers' block sends her down memory lane to Richard's first day on the job---a day with trouble in store for Caroline because she and Del had just rekindled their romance.
#2 - Pilot
Season 1 - Episode 1 - Aired 9/21/1995
Caroline hires Richard as her new colorist, and takes Annie's advice to try getting a date by throwing fruit out her window.
#3 - Caroline and the Return of the Sudsy Guy (1)
Season 4 - Episode 19 - Aired 3/29/1999
Sparks fly between Caroline and Randy when he pays her a surprise visit in New York and they end up getting stuck together in a subway tunnel for two hours. Meanwhile, Richard gets his first real break as an artist when an eccentric gallery owner offers to exhibit his work -- but only if he can create another 'bleak' painting in time for the next day's show.
#4 - Caroline and the 2000th Strip
Season 4 - Episode 17 - Aired 3/8/1999
There's to be a big celebrity banquet to celebrate Caroline's 2000th strip, but there's a snag: Caroline is completely blocked in terms of fresh, funny ideas. While everyone else waits for her to get ready (Richard in a cheap rental tuxedo which gradually disintegrates), Caroline fantasizes about what life would be like if she retired. When she tearfully refuses to attend the banquet and does laundry instead, Richard gently points out that she has stopped writing about her real life in the strip (her fictional counterpart is ""still dating that veterinarian"") and perhaps it is time to bring her readers up to date -- and Caroline immediately draws a strip about their first date on the side of the washing machine.
#5 - Caroline and the Freight King
Season 2 - Episode 11 - Aired 12/17/1996
When a doodle of a porcupine drawn by Richard gets into a stack of Caroline's greeting card designs by mistake, Del tries to convince Richard to develop the idea into a character of his own - but Richard protests that he is a real artist, not a cartoonist, throwing Caroline for a loop. Annie can't seem to shake a recurring five dollar bill with ""Repent"" written on it, and her mother tries to convince her it's a sign from God that she should return to the Church. When Caroline accidentally gets locked inside the laundry room overnight, her encounter with a bum who used to be a trucking magnate convinces her she has made the right career choice. Richard succumbs to Del's monetary temptation and produces a series of increasingly gloomy and unusable porcupine cards; and he finally apologizes and admits that he admires Caroline's professionalism as a cartoonist. Meanwhile, when a telegram stripper shows up at Del's office by mistake (she was supposed to be at a law firm), Del hires her as r
#6 - Caroline and the Dreamers
Season 2 - Episode 5 - Aired 10/29/1996
Del starts his own greeting card company, Eagle Greeting Cards, and Caroline reluctantly joins. Meanwhile, Richard is chosen to paint a mural for the city, which turns out to be in a shady part of town.
#7 - Caroline and the Letter (2)
Season 2 - Episode 2 - Aired 9/24/1996
Realizing Caroline never received his love letter, Richard labors to retrieve it from her friend's apartment.
#8 - Caroline and the Younger Man (1)
Season 2 - Episode 1 - Aired 9/17/1996
Three months have passed, and Caroline is thinking about advertising for a new assistant, so Charlie tries to demonstrate he would be perfect for the job and knocks Salty out the window. Sparks fly between Caroline and the vet who treats Salty, despite her fears that at 24 he is much too young for her. Meanwhile Richard, having failed as an artist in Paris (his only customer is knocked into the Seine just before buying some paintings), returns to New York and is forced to take a menial job in an ice cream parlor, where he just misses seeing Caroline on her first date with Joe, during which they helped raid an animal experimental laboratory and were arrested. (One of the participants is Shelly, still wistful about Richard, in her final appearance to date.) Caroline wakes up in bed with Joe and is unable to sneak out before he wakes and demands to see her again that evening, and on her way home she and Richard suddenly meet face to face.
#9 - Caroline and the Bridesmaid
Season 1 - Episode 22 - Aired 5/9/1996
Preparations for the wedding cause friction between Caroline and Annie, who can't seem to take her responsibilities as maid of honor seriously.
#10 - Caroline and the Movie
Season 1 - Episode 19 - Aired 4/4/1996
Caroline, Richard and Annie are cast as extras in a film, leading to some surprising developments for its star (Benson) and director (Landis) when Annie turns out to be a Benson fanatic - and Richard becomes insanely jealous of the extra who is to kiss Caroline. Meanwhile, Del's Porsche is towed, and when he claims it from the DMV, he gets someone else's Gremlin instead. When he tracks down the Gremlin's owner, the poor man pleads for more time - he's got a hot date with a woman who was really only impressed by the Porsche.
#11 - Caroline and the Ex-Wife
Season 1 - Episode 18 - Aired 3/28/1996
Del and Caroline's vacation takes an unexpected turn when they run into Del's bitter ex-wife Jill at his cabin. Meanwhile, Annie's brother Pete decides to quit the family business, which doesn't sit well with his parents.
#12 - Caroline and the Gay Art Show
Season 1 - Episode 3 - Aired 10/5/1995
Richard takes his paintings out of the closet when Caroline and Annie convince a gallery owner to consider them for an exclusive show - which turns out to be for gay artists only; Annie becomes entangled in Caroline's search for a new hair dresser - and her old hairdresser (Lerner) spots her at the gallery opening party.
#13 - Caroline and the Bad Back
Season 1 - Episode 4 - Aired 10/12/1995
Richard and Del bend over backwards to help an injured Caroline complete her work in time for a deadline, but things go from bad back to worse when medication dulls her pain - and her mind - so Richard and Del have to finish the strip for her.
#14 - Caroline and the ATM
Season 1 - Episode 5 - Aired 10/19/1995
Being too picky could cost Caroline the chance to reclaim money she lost at a malfunctioning ATM, since she doesn't really want to bank staff to see her picking her nose on the videotape record of the transaction. Meanwhile, Richard may end up in the doghouse after he attempts to dump the clinging Shelly on the pretext that he is allergic to her beloved dog.
#15 - Caroline and Richard's Mom
Season 1 - Episode 21 - Aired 4/25/1996
Richard faces some childhood traumas when his mother (Ashley) makes a surprise visit: it seems she is given to claiming to know celebrities personally, and Richard has never quite gotten over her promise to have Salvador Dali look at his paintings. But Caroline doesn't know this when Natalie promises to get her own NBC Saturday morning cartoon show.
#16 - Caroline and the Cat Dancer
Season 2 - Episode 3 - Aired 10/15/1996
Richard tries to adjust to his new apartment, where he is plagued by noisily amorous neighbors; Joe tries to adjust to the fact that Caroline plans to remain friends with Del; and Annie frantically tries to adjust her financial records when she is notified that the IRS is auditing her for 1993, a year she barely remembers. Her bad-tempered auditor is under fire for being too lenient with his clients, but when he learns she is a dancer in Cats, he strikes a deal: she'll ""never have to pay taxes again"" if she can get him an audition for the show. Enter 'producer' Del and 'director' Charlie. Meanwhile, disturbed by Joe's jealousy, Caroline makes up her mind to break a date with Del by telling him she's been called out of town.
#17 - Caroline and the Therapist
Season 2 - Episode 9 - Aired 12/3/1996
When Salty begins behaving oddly, Joe recommends that Caroline consult a cat therapist, who decides it's really Richard who needs help.
#18 - Caroline and the Ultimatum (2)
Season 4 - Episode 20 - Aired 4/5/1999
Caroline gives Richard a matrimonial ultimatum; but on his way to propose to her, he is taken hostage in a video store holdup. He decides that escape will prove his manhood and worthiness of Caroline -- and when he is wheeled in by paramedics, he does indeed propose.
#19 - Caroline and the Nice Jewish Boy
Season 2 - Episode 6 - Aired 11/12/1996
Joe refuses to accompany Caroline to an award ceremony because one of the sponsors makes mink coats. Meanwhile, Del lies about his background to date an attractive woman whose parents will only allow her to date Jewish men.
#20 - Caroline and the Comic
Season 2 - Episode 8 - Aired 11/26/1996
Richard's father asks for his son's help in reviving an old comedy routine.
#21 - Caroline and the Guy Who Gets There Too Soon
Season 2 - Episode 4 - Aired 10/22/1996
When Caroline's young, new boyfriend says 'I love you' far too soon, she decides they should see other people. Meanwhile, Annie agrees to teach Richard how to drive after he inherits his aunt's car.
#22 - Caroline and the Opera
Season 1 - Episode 7 - Aired 11/9/1995
Caroline is annoyed that Del refuses to accompany her to the opera; then her interfering Aunt Mary arranges a blind date with an old high school classmate of Caroline's, who turns out to be handsome, successful and rich.
#23 - Caroline and the Folks
Season 1 - Episode 6 - Aired 11/2/1995
Caroline must face dinner at Remo's with Del's parents alone when Del doesn't show up; Del is trapped on a stalled subway with Charlie, who insists on sharing his ideas for greeting cards for pets; and Richard's non-plans for his 30th birthday change when Annie visits to exchange swapped video rentals.
#24 - Caroline and the Wedding
Season 1 - Episode 23 - Aired 5/16/1996
An ominous dream, an inexperienced priest and a surprising love letter threaten Caroline's wedding.
#25 - Caroline and Victor/Victoria
Season 2 - Episode 7 - Aired 11/19/1996
Annie poses as a man to prepare for a ""Victor/Victoria"" audition.