Caroline in the City

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.

Last Updated: 7/24/2022Network: NBC
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Caroline and the Wayward Husband (3)
star
10.00
1 votes

#1 - Caroline and the Wayward Husband (3)

Season 2 - Episode 25 - Aired 5/13/1997

Conclusion. Julia arrives at ""Richard and Caroline's"" apartment in tears, announcing that her engagement is over and demanding to spend the night on the sofa - which means Richard and Caroline have to spend the night together in her bedroom. A nude Julia reveals that seeing the happy couple has revived her feelings for a non-plussed Richard; meanwhile, Caroline consults Del about the possibility of a relationship with Richard, and an uncharacteristically thoughtful Del advises her to follow her heart. Annie's first day on the set of the Shadoe Stevens series doesn't go well, as she is totally unable to master her complicated medical lines, until the director and writer agree to switch her to the part of the hard-bitten female cop (resulting in even more unspeakable jargon). Del is in despair over the impending loss of his company, until Charlie bails him out with the trust find his father has maintained for him all these years - on condition that he becomes Del's partner. Caroline phon

Directors: Will Mackenzie
Watch Now:Amazon
Caroline and the Love That Dares Not Speak its Name
star
9.00
2 votes

#2 - Caroline and the Love That Dares Not Speak its Name

Season 3 - Episode 13 - Aired 1/5/1998

Caroline is aghast that Annie blabbed to Richard about her feelings for him, and tries to avoid his questions by inviting in a hyper-anxious knife salesman. When Richard discovers the truth about the answering machine message Caroline left for him (and which Julia erased), the two finally confess their mutual attraction, but quickly agree that they have both moved on. But a dinner double date at Caroline's turns into a competition for happiest couple between Caroline & Trevor and Richard & Julia - until they all wind up in an emergency ward with food poisoning from Caroline's fish chowder. Meanwhile, Annie tries a song and dance routine to help Del and Charlie defend their greeting card trade show turf against Del's evil brother Garner.

Directors: James Burrows
Watch Now:Amazon
Caroline and the Secret Bullfighter (2)
star
8.50
2 votes

#3 - Caroline and the Secret Bullfighter (2)

Season 3 - Episode 26 - Aired 5/18/1998

On the eve of their moving in together, Caroline leaves Trevor alone as she dashes off to Spain, with Annie in tow, in an attempt to repair the damage she has done to Richard and Julia's marriage. Lunching at Remo's, they have seen Remo's new waitress wearing a diamond bracelet and realized it was she making love to José during the party. Richard arrives in Spain and the hotel maid, who hates Julia, directs him to the ""matador bar"" on the corner; but when he demands to speak to a ""worthless matador named José,"" every man in the bar stands up. By the time Caroline and Annie arrive, Richard has traced Julia to Pamplona, where she has gone to see the running of the bulls; unaware of the event, and distracted by the arrival of Caroline, Richard flees for his life and is trampled by the bulls - only mildly, as we discover. Meanwhile, Del suffers through endless bad pitches thrown by Monica's son while Charlie explains why he won't let the hopeless kid into the game, and discovers an unexpec

Directors: Michael Zinberg
Caroline and the Guys in the Bathroom
star
8.20
5 votes

#4 - Caroline and the Guys in the Bathroom

Season 4 - Episode 1 - Aired 9/21/1998

Acting as narrator, the Elevator Lady brings us up to speed on the events at last season's close culminating in Richard and Caroline's first kiss. Desperately aroused, Caroline and Richard pause only long enough for Caroline to run to the bathroom to brush her teeth; but once there she is confronted by a vision of four men: ex-boyfriend Trevor, the first man she ever slept with, the high school coach she had a crush on, and the first little boy she ever kissed. An angry dialogue ensues, and an inflamed Richard, overhearing, strips down - only to be walked in on by an angry Annie, who accuses him of exploiting Caroline's vulnerable state. Then Caroline emerges from the bathroom naked, only to be confronted by Annie and Charlie, the latter having arrived with an urgent message from Del: Eagel Greeting Cards is going out of business. A mortified Caroline dresses and rushes to comfort Del, only to discover that he is celebrating the sale of his company to a major conglomerate, and to be pr

Directors: Ted Wass
Watch Now:Amazon
Caroline and the Proposal
star
8.00
5 votes

#5 - Caroline and the Proposal

Season 1 - Episode 16 - Aired 2/22/1996

When Richard learns of Del's proposing to Caroline, he goes searching for another job, and is seduced by his just-divorced employment counselor; Remo and Annie try to convince a skeptical Caroline that she's oblivious to Richard's feelings for her - and hers for him.

Directors: James Burrows
Watch Now:Amazon
Caroline and the Buyer
star
8.00
4 votes

#6 - Caroline and the Buyer

Season 2 - Episode 19 - Aired 4/1/1997

Del asks Caroline to help him woo one of his father's biggest clients, a greeting-card store magnate who misunderstands what the cartoonist has to offer. Meanwhile, Annie resents Richard's relationship with her mother, and a friendly game of bocci turns ugly.

Directors: Will Mackenzie
Watch Now:Amazon
Caroline and the Decanter
star
8.00
2 votes

#7 - Caroline and the Decanter

Season 3 - Episode 12 - Aired 12/15/1997

When Caroline's parents are stranded in Wisconsin by a snowstorm, Caroline reluctantly accompanies Del to his dysfunctional family Christmas - especially after he tells her that his mother still resents her never having brought a hostess gift the first time they met - leaving Charlie to house-sit Salty and attempt to spend some quality holiday time with his father. Meanwhile, while Richard tries to be enthusiastic about a delayed honeymoon trip to Hawaii, Annie tries to help Julia overcome her fear of flying with some tranquilizers that work all too well - and while defending herself to a furious Richard, lets slip the little fact that Caroline is ""still"" in love with him....

Directors: Will Mackenzie
Caroline and the Condom
star
7.86
36 votes

#8 - 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.

Directors: James Burrows
Watch Now:Amazon
Caroline and the Monkeys
star
7.67
3 votes

#9 - Caroline and the Monkeys

Season 2 - Episode 18 - Aired 3/11/1997

Del hopes to spark up romance with Annie's neurotic friend Cassandra, who plans on lighting a fire of her own - she's a compulsive pyromaniac just of an institution. Meanwhile, Caroline spends a night out on the town ""alone,"" crashing the restaurant where Richard is trying to enjoy a quiet meal and ultimately being forced by him to attend a movie on her own. Meanwhile, Charlie keeps spotting monkeys throughout Manhattan, and becomes convinced they are taking over the city.

Directors: Andrew Tsao
Watch Now:Amazon
Caroline and the Booby Trap
star
7.67
3 votes

#10 - Caroline and the Booby Trap

Season 4 - Episode 9 - Aired 11/30/1998

After Annie is beaten out in an audition by an untalented but well endowed rival, she announces her intention to have breast augmentation surgery during a Thanksgiving dinner already complicated by Del's turning up with a frozen rather than pre-cooked turkey and the bizarre behavior of mailroom Dave. Unable to talk Annie out of it, Caroline then beats her to the doctor's office to consider treatment herself after Richard's ill-timed admission that he has fantasized about her with larger breasts. A fantasy sequence in which Caroline imagines special treatment aboard a plane convinces her to stay with what she's got. Meanwhile, Richard has taken Caroline's riposte (that she has imagined him with darker, sexier hair) to heart, but when Del's current girlfriend shows up to rescue him from the effects of an amateurish home dye job, she realizes Del stood her up for Thanksgiving and storms out, leaving Richard to deal with a bad case of chemically induced hair loss.

Directors: Ted Wass
Watch Now:Amazon
Caroline and the Married Man
star
7.57
7 votes

#11 - Caroline and the Married Man

Season 1 - Episode 12 - Aired 1/11/1996

Richard sets Caroline up on a date with a man (Gravitte) who can get him a civic commission for an important mural, and they hit it off; then Richard discovers the guy is married.

Directors: Tom Cherones
Watch Now:Amazon
Caroline and the Singer
star
7.50
4 votes

#12 - Caroline and the Singer

Season 2 - Episode 13 - Aired 1/14/1997

Annie's sister Donna, who has come to town in hopes of reviving her singing career, discovers Richard's secret love letter to Caroline (inside Annie's diary) and uses it as inspiration for a new song, to Richard's horror and Annie's fury, since she has been using the letter to blackmail Richard into taking her mother to electrolysis appointments. Caroline is preoccupied with her perfect plain black pumps, which she left in Joe's apartment; after a fruitless quest to replace them, she sneaks in to retrieve them, and is found by a repentant Joe. Meanwhile, Del and Charlie get snowed in - inside Del's Porsche, with the keys and his cell phone locked in the trunk by Charlie.

Directors: Will Mackenzie
Watch Now:Amazon
Caroline and the Free Cable
star
7.50
2 votes

#13 - Caroline and the Free Cable

Season 3 - Episode 4 - Aired 10/13/1997

Julia throws a surprise birthday party for Richard by inviting everyone in his address book, under the impression that they are his friends, which results in a gathering chiefly of his ex-therapists - one of whom is interested in Annie, to Richard's horror. Meanwhile, the discovery that she has been getting illegal free cable for years puts Caroline in a moral spin, since the rest of the building is hooked into her outlet and anxious for her not to do the right thing.

Directors: Andrew Tsao
Watch Now:Amazon
Caroline and the Egg
star
7.50
2 votes

#14 - Caroline and the Egg

Season 3 - Episode 6 - Aired 11/3/1997

Caroline's former colorist Jeannie comes back to town on a mission: she and her husband can't conceive, so she wants Caroline to donate an egg; Annie naturally seizes the opportunity to make Richard paranoid that Caroline plans to re-hire Jeannie. Meanwhile, Del has a close encounter with his old Porsche and gets himself hired as a male escort for the company that now owns his former automotive love.

Directors: Arlene Sanford
Watch Now:Amazon
Caroline and the Councilman
star
7.50
2 votes

#15 - Caroline and the Councilman

Season 3 - Episode 10 - Aired 12/1/1997

Del gets excited over commercial possibilies when a civic politican mentions Caroline's cartoon strip in a speech, but Richard pours cold water on the idea: the man has a terrible record for opposing funding for the arts. His opinon changes slightly when Del drags the wily politico over for a meeting, whereupon Lake goes wild over Richard's recently completed painting and buys it. By the time Richard thinks better of selling his first work to a man he despises, Julia has already spent the money on a honeymoon trip to Hawaii; so Caroline steps in to prove she is not as politically naive as everyone assumes. Meanwhile, Annie, trying to cope with her cousin Jennifer who has dropped out of high school to find an acting career in Manhattan, goes ballistic when she discovers the girl has met a man claiming to be a movie producer who has promised her a role opposite Keanu Reeves - and sets out for the guy's hotel room to tell him off....

Directors: James Burrows
Watch Now:Amazon
Caroline and the Reluctant Father
star
7.50
2 votes

#16 - Caroline and the Reluctant Father

Season 3 - Episode 15 - Aired 1/19/1998

An unusual episode focussing on Del, who for once has an adult problem after he hears some shocking news from Laura, a former fling who's in town for the weekend - together with the daughter she had by Del but never told him about. Torn between a burning desire to meet his child and his terror of being a total disappointment to her, and Annie's brother quits his job to become a painter after he misinterprets Richard's evaluation of his work as an artist.

Directors: Peter Chakos
Watch Now:Amazon
Caroline and the New Neighbor
star
7.33
3 votes

#17 - Caroline and the New Neighbor

Season 2 - Episode 20 - Aired 4/8/1997

Things get a little stiff when an demanding elderly new neighbor, who is driving an initially sympathetic Caroline nuts, asks Caroline and Annie for a really big favor - to help out with the removal of her dead, naked husband. Meanwhile, Richard tries to sell his car, but the only bidder is Louis, a bizarre individual claiming to be a minister and promising eternal life in exchange for the vehicle. Charlie, smitten with Sophia, the beautiful new waitress at Remo's, offers Richard $500 (which he makes driving the car as a gypsy cab) so he can give the car to Sophia as a love token; but Richard decides to keep the car and drive it as a cab himself. Through all this, Del is obsessed with the idea that he is losing his hair and his looks.

Directors: Michael Zinberg
Watch Now:Amazon
Caroline and the Bar Mitzvah
star
7.33
3 votes

#18 - Caroline and the Bar Mitzvah

Season 4 - Episode 10 - Aired 12/14/1998

Richard's Aunt Frieda announces that before she moves to Florida and wants to see Richard go through with the bar mitzvah he abandoned, and is willing to pay him $5,000 for the privilege. While an embarrassed Richard returns to Hebrew school, Caroline and Annie prepare a mocking party in his honor -- until Richard confesses to Caroline that he is doing it for the money only because he is humiliated by her having to pick up the tab for everything they do together. Meanwhile, Del gets a great deal in expensively tailored Italian suits, but won't admit they are several sizes too small for him.

Directors: Brent Carpenter
Caroline and the Getaway
star
7.25
4 votes

#19 - Caroline and the Getaway

Season 2 - Episode 17 - Aired 2/25/1997

When Caroline calls her out on always blowing her off for male dates, Annie makes a deal: they will go away together for a weekend skiing trip and ignore men. Naturally, both immediately spot exceptionally interesting men: an old school chum of Caroline's who confesses to having had a mutual crush, and for Annie a handsome tycoon. Meanwhile, Richard is hoping that his relationship with a fellow philosophy student won't remain Platonic, but the tryst he arranges in Caroline's apartment while she is away is invaded by Del and Charlie, who intend to make themselves at home to watch sports.

Directors: James Burrows
Watch Now:Amazon
Caroline and the Paper Chase
star
7.25
4 votes

#20 - Caroline and the Paper Chase

Season 4 - Episode 6 - Aired 11/2/1998

Del has hired Caroline and Annie to provide the voices for his new promotional video, but when he comes to pick them up it turns out they have to perform it for the boss first as a puppet show - about menstruation. While Annie is in her office, Caroline searches in Richard's desk for a highlighter and finds his divorce papers, and Richard angrily denounces her invasion of his privacy. Of course Annie immediately lifts the papers, is forced to hide them from Richard, sees them dumped down the corporate mail chute, and has to enlist Caroline's help to wheedle them back from the bizarre and hostile mail room staff - leaving a reluctant Richard and a strangely eager Charlie to act out the puppet show for Mr. MacDermott, who reveals that he is only doing the animated cartoon as part of a community service sentence. Discovering that the divorce papers are two months old but that Richard has not yet signed them, and is therefore technically still married, Caroline confronts him - and he confe

Directors: Ted Wass
Watch Now:Amazon
Caroline and the Big Night
star
7.25
4 votes

#21 - Caroline and the Big Night

Season 4 - Episode 7 - Aired 11/9/1998

Caroline and Richard's big night finally arrives, in the form of a romantic weekend booked in the perfect room at the perfect country bed and breakfast. What's wrong with this picture? Naturally everything: Richard's choice of the perfect negligée for Caroline to wear gets switched for Del's brother's barbeque apron; their room is given away to another couple who have gotten married after not seeing each other for 30 years; and the bed and breakfast is run by a bitter, bickering pair of neurotics who ultimately throw Caroline and Richard out. But Richard saves the day by getting Annie and Del to turn Caroline's apartment into a romantic fantasyland - which, we learn in the coda, they enjoy for several consecutive days...

Directors: Howard Deutch
Watch Now:Amazon
Caroline and the Dearly Departed
star
7.20
5 votes

#22 - Caroline and the Dearly Departed

Season 2 - Episode 16 - Aired 2/18/1997

It's not a pretty picture when Caroline persuades reluctant con-artist Richard to fake his own death in order to catch the eye of a wealthy art dealer who's scouring the city in search of the works of dead painters - and who winds up delivering the eulogy at Richard's fake funeral.

Directors: James Burrows
Watch Now:Amazon
Caroline and the Mugger
star
7.14
14 votes

#23 - Caroline and the Mugger

Season 1 - Episode 2 - Aired 9/28/1995

Richard is mugged and robbed of his wallet and portfolio - containing Caroline' s drawings.

Directors: James Burrows
Watch Now:Amazon
Caroline and the Letter (2)
star
7.14
36 votes

#24 - 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.

Directors: Gordon Hunt
Watch Now:Amazon
Pilot
star
7.12
51 votes

#25 - 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.

Directors: James Burrows
Watch Now:Amazon

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