The BEST Episodes of Caroline in the City

Every episode ever - ranked by fan votes!

Last Updated: Sep 24, 2020

Network: NBC

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.

Caroline and the Wayward Husband (3)

#1 - Caroline and the Wayward Husband (3)

Season 2 - Episode 25 - Aired May 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

star 10.00
1 votes
Directors: Will Mackenzie
Writers: Kim Friese
Caroline and the Secret Bullfighter (2)

#2 - Caroline and the Secret Bullfighter (2)

Season 3 - Episode 26 - Aired May 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

star 10.00
1 votes
Directors: Michael Zinberg
Writers: Michael Sardo
Caroline and the Love That Dares Not Speak its Name

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

Season 3 - Episode 13 - Aired Jan 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.

star 9.00
2 votes
Directors: James Burrows
Writers: Brian Hargrove, Jack Kenny
Caroline and the Diva

#4 - Caroline and the Diva

Season 4 - Episode 8 - Aired Nov 16, 1998

Jealousy between Richard and Annie reaches a new height when Richard wants to attend an operatic recital to which Caroline invited Annie months ago. The two squabble so childishly that an infuriated Caroline tells them off loudly - and the insulted diva walks off the stage and refuses to return. When Caroline sneaks into the star's dressing room to apologize and beg her to finish the recital, she winds up rubbing her feet and getting drunk with her on champagne, and returns home to find that Richard and Annie's mutual anxiety about her whereabouts has produced a sort of truce. Meanwhile, Del finds himself taking a reluctant ethical stance when he is invited to an executive charter jet weekend on condition that he persuades cartoonist Reg to introduce a white character into his black-only post-apocalyptic fantasy world; and a furtive pair of nerdish animators fall madly in love with Caroline but are unable to speak in her presence.

star 9.00
1 votes
Directors: Howard Deutch
Writers: Jim Keily, Jimmy Aleck
Caroline and the Fright Before Christmas

#5 - Caroline and the Fright Before Christmas

Season 4 - Episode 11 - Aired Dec 21, 1998

Richard, Del and Annie are apparently successful in their combined effort to knock the Christmas spirit out of Caroline, but when she appears to have lost all interest in her annual tree-trimming festivities, her alarmed buddies declare an emergency trip to nearby ""Christmasville,"" only to discover that Caroline engineered the whole thing. When even the local re-enactment of A Christmas Carol doesn't do the trick, a furious Caroline tries to drive away and backs into the town's main transformer, blacking out all of ""Christmasville"" and condemning them to slave off their sentence in Santa's workshop.

star 9.00
2 votes
Directors: Ted Wass
Writers: Oliver Goldstick
Caroline and the Horny Kid

#6 - Caroline and the Horny Kid

Season 4 - Episode 13 - Aired Jan 18, 1999

Del and Caroline participate in the company's mentoring program, but Caroline's adolescent charge Stan develops an embarrassing crush on her, while Del's turns into a teenage fixer who takes over Del's professional and personal lives with impressive competence. Meanwhile, Reg tries to convince Richard to sell his art, but the results are disastrous: a coffee house show is a fiasco, and when Richard desperately tries to emulate a subway hawker and sell his works to consumers, he is busted by an undercover cop who confiscates his art.

star 9.00
1 votes
Directors: Ted Wass
Writers: Tom Burkhard
Caroline and the Guys in the Bathroom

#7 - Caroline and the Guys in the Bathroom

Season 4 - Episode 1 - Aired Sep 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

star 8.75
4 votes
Directors: Ted Wass
Writers: Michael Sardo
Caroline and the Proposal

#8 - Caroline and the Proposal

Season 1 - Episode 16 - Aired Feb 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.

star 8.00
3 votes
Directors: James Burrows
Writers: Fred Barron, Ian Praiser, Marco Pennette
Caroline and the Buyer

#9 - Caroline and the Buyer

Season 2 - Episode 19 - Aired Apr 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.

star 8.00
3 votes
Directors: Will Mackenzie
Writers:
Caroline and the New Neighbor

#10 - Caroline and the New Neighbor

Season 2 - Episode 20 - Aired Apr 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.

star 8.00
2 votes
Directors: Michael Zinberg
Writers: Christopher Fife
Caroline and the Free Cable

#11 - Caroline and the Free Cable

Season 3 - Episode 4 - Aired Oct 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.

star 8.00
1 votes
Directors: Andrew Tsao
Writers: Nancy Steen
Caroline and the Egg

#12 - Caroline and the Egg

Season 3 - Episode 6 - Aired Nov 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.

star 8.00
1 votes
Directors: Arlene Sanford
Writers: Nancy Steen
Caroline and the Councilman

#13 - Caroline and the Councilman

Season 3 - Episode 10 - Aired Dec 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....

star 8.00
1 votes
Directors: James Burrows
Writers: Lester Lewis
Caroline and the Decanter

#14 - Caroline and the Decanter

Season 3 - Episode 12 - Aired Dec 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....

star 8.00
1 votes
Directors: Will Mackenzie
Writers: Deborah Zoe Dawson, Jodie Mann Massimi
Caroline and the Booby Trap

#15 - Caroline and the Booby Trap

Season 4 - Episode 9 - Aired Nov 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.

star 8.00
2 votes
Directors: Ted Wass
Writers: Marcy Vosburgh
Caroline and the Bar Mitzvah

#16 - Caroline and the Bar Mitzvah

Season 4 - Episode 10 - Aired Dec 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.

star 8.00
2 votes
Directors: Brent Carpenter
Writers: Jason Strouse
Caroline and the Big Bad Bed

#17 - Caroline and the Big Bad Bed

Season 4 - Episode 12 - Aired Jan 11, 1999

Caroline becomes upset over what she sees as Richard's refusal to share his private life with her -- which comes to a head when Reg Preston's girlfriend kicks him out and he moves in temporarily with Richard. Meanwhile, Del and Annie forge a temporary truce and attempt to find dates for each other at the gym. Del strikes out, but Annie finds an obliging man mountain she'd ""like to hire a team of sherpas and climb.""

star 8.00
1 votes
Directors: Ted Wass
Writers: Gary Murphy, Neil Thompson
Caroline and the Firing Squad

#18 - Caroline and the Firing Squad

Season 4 - Episode 14 - Aired Jan 25, 1999

Caroline is appalled to discover that Del (currently obsessed with buying a new Porsche) is paying his partner Charlie to stay at home so that his bizarre ideas won't compromise Del's career. When she persuades Del to let Charlie attend a planning meeting, the plan backfires big time: Charlie is fired. Charlie decides he wants to travel in Europe, and Del does the right thing and gives him the money for his Porsche as severance. Meanwhile, Richard gets Annie a job posing for a cartoonist who starts dating her, but the deal is fishy: it turns out he is only interested in her when she is dressed as the bizarre science fiction heroine of his strip.

star 8.00
1 votes
Directors: Shelley Jensen
Writers: Jim Keily, Jimmy Aleck
Caroline and the Condom

#19 - Caroline and the Condom

Season 1 - Episode 24 - Aired Aug 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.

star 7.91
35 votes
Directors: James Burrows
Writers: Fred Barron, Marco Pennette
Caroline and the Singer

#20 - Caroline and the Singer

Season 2 - Episode 13 - Aired Jan 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.

star 7.67
3 votes
Directors: Will Mackenzie
Writers: Brian Hargrove, Jack Kenny
Caroline and the Big Night

#21 - Caroline and the Big Night

Season 4 - Episode 7 - Aired Nov 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...

star 7.67
3 votes
Directors: Howard Deutch
Writers: Tom Burkhard
Caroline and the Married Man

#22 - Caroline and the Married Man

Season 1 - Episode 12 - Aired Jan 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.

star 7.60
5 votes
Directors: Tom Cherones
Writers: Wil Calhoun
Caroline and the Paper Chase

#23 - Caroline and the Paper Chase

Season 4 - Episode 6 - Aired Nov 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

star 7.33
3 votes
Directors: Ted Wass
Writers: Arlene Hellerman
Caroline and the Mugger

#24 - Caroline and the Mugger

Season 1 - Episode 2 - Aired Sep 28, 1995

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

star 7.25
12 votes
Directors: James Burrows
Writers: Dottie Dartland
Pilot

#25 - Pilot

Season 1 - Episode 1 - Aired Sep 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.

star 7.21
48 votes
Directors: James Burrows
Writers: Dottie Dartland, Fred Barron, Marco Pennette