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The Best Episodes of Caroline in the City

Every episode of Caroline in the City ranked from best to worst. Let's dive into the Best Episodes of Caroline in the City!

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Caroline in the City is an American situation comedy that ran on the NBC television network. It stars Lea Thompson as cartoonist Caroline Duffy, who lives in Manhattan in New York City. The series premiered

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Episode Rankings

  1. #1 Fan Favorite
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    Caroline in the City Season 1 Episode 18 - Caroline and the Ex-Wife
    8.0/10(134 votes)

    #1 - Caroline and the Ex-Wife

    S1:E18

    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.

    Director:Tom Cherones
    Writer:Unknown

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  2. Caroline in the City Season 2 Episode 25 - Caroline and the Wayward Husband (3)
    7.7/10(55 votes)

    #2 - Caroline and the Wayward Husband (3)

    S2:E25

    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

    Director:Will Mackenzie
    Writer:Kim Friese

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  3. Caroline in the City Season 2 Episode 24 - Caroline and Richard & Julia (2)
    7.6/10(58 votes)

    #3 - Caroline and Richard & Julia (2)

    S2:E24

    Richard's long-lost love arrives with bad news: she's getting married in two days, to arrogant and insanely jealous fashion designer Marcello. Not to be outdone, Richard concocts a coupling of his own - to Caroline, much to her astonishment. Meanwhile, Del's business is going bankrupt, so he reluctantly arranges a midnight meeting at Remo's with his arrogant father, who refuses to help him but does buy Del's Porsche at an instant profit to teach him a lesson. Annie is offered a part in a pilot for a new series starring Shadoe Stevens, and instantly calls New York to resign from Cats.

    Director:Will Mackenzie
    Writer:Bill Masters

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  4. Caroline in the City Season 1 Episode 1 - Caroline in the City
    7.5/10(101 votes)

    #4 - Caroline in the City

    S1:E1

    Caroline hires Richard as her new colorist, and takes Annie's advice to try getting a date by throwing fruit out her window.

    Director:James Burrows
    Writers:Marco Pennette, Fred Barron, Dottie Dartland Zicklin

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  5. Caroline in the City Season 1 Episode 11 - Caroline and the Gift
    7.5/10(65 votes)

    #5 - Caroline and the Gift

    S1:E11

    Del's unexpectedly generous Christmas gift - a pair of ugly but valuable earrings - makes Caroline question his intentions. Richard paints a commissioned nude portrait of a beautiful woman (Udenio) who has a well-connected husband - well -connected in ""the Family,"" according to a frightened Remo. And Annie can't remember her New Year's Eve party at which she met a man who has since telephoned her to confirm their date.

    Director:James Burrows
    Writer:Bill Prady

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  6. Caroline in the City Season 1 Episode 16 - Caroline and the Proposal
    7.5/10(66 votes)

    #6 - Caroline and the Proposal

    S1:E16

    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.

    Director:James Burrows
    Writers:Marco Pennette, Fred Barron

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    The 20 WORST Episodes of Caroline in the City

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  7. Caroline in the City Season 1 Episode 23 - Caroline and the Wedding
    7.5/10(65 votes)

    #7 - Caroline and the Wedding

    S1:E23

    An ominous dream, an inexperienced priest and a surprising love letter threaten Caroline's wedding.

    Director:James Burrows
    Writer:Bill Masters

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  8. Caroline in the City Season 1 Episode 14 - Caroline and the Watch
    7.4/10(70 votes)

    #8 - Caroline and the Watch

    S1:E14

    Caroline finds a watch in her new antique desk and tries to find its previous owners; meanwhile, Del learns that a deceased employee was an embezzler.

    Director:James Burrows
    Writer:Mark Wilding

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  9. Caroline in the City Season 1 Episode 3 - Caroline and the Gay Art Show
    7.3/10(71 votes)

    #9 - Caroline and the Gay Art Show

    S1:E3

    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.

    Director:James Burrows
    Writer:Unknown

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  10. Caroline in the City Season 2 Episode 3 - Caroline and the Cat Dancer
    7.3/10(65 votes)

    #10 - Caroline and the Cat Dancer

    S2:E3

    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.

    Director:Michael Lembeck
    Writers:Brian Hargrove, Jack Kenny

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  11. Caroline in the City Season 2 Episode 6 - Caroline and the Nice Jewish Boy
    7.3/10(59 votes)

    #11 - Caroline and the Nice Jewish Boy

    S2:E6

    Joe refuses to accompany Caroline to an award ceremony because one of the sponsors uses animal products; so she calls former date Willard, whom she dumped because he was fat and balding. After Charlie takes him to a Jewish singles event by mistake, Del lies about his background to date an attractive woman who parents will only allow her to date Jewish men. Willard shows up a reformed hunk who only came to tell Caroline to go to hell - ""And I'm rich, too!"" Aghast that Del plans to tell Risa the truth only after they spend a weekend together, Caroline points out delicately that if they sleep together Risa will know only, because Del is a ""turtleneck kind of guy."" So Del books himself into hospital, telling Risa he needs his ""tonsils"" removed; but she shows up to confess that she is eloping with her former boyfriend, who isn't Jewish either. A reluctant Richard escorts Caroline and even more reluctantly dances with her. Just as they seem about to have a tender moment, Joe appears, having

    Director:Will Mackenzie
    Writer:Tom Leopold

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  12. Caroline in the City Season 2 Episode 8 - Caroline and the Comic
    7.3/10(57 votes)

    #12 - Caroline and the Comic

    S2:E8

    Richard's father asks for his son's help in reviving an old comedy routine.

    Director:Howard Deutch
    Writers:Marco Pennette, Fred Barron

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  13. Caroline in the City Season 2 Episode 13 - Caroline and the Singer
    7.3/10(61 votes)

    #13 - Caroline and the Singer

    S2:E13

    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.

    Director:Will Mackenzie
    Writers:Brian Hargrove, Jack Kenny

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  14. Caroline in the City Season 3 Episode 1 - Caroline and the Reception (4)
    7.3/10(57 votes)

    #14 - Caroline and the Reception (4)

    S3:E1

    An anxious Caroline, not aware that Julia intercepted his message, waits for Richard's response but isn't prepared for his ""Oh, why is it so difficult to say three words - I got married!"" Devastated, Caroline calls Del in the middle of the night and he rushes over - still handcuffed to his date Kristin, and must be released by an amused Annie with one of her collection of keys. Caroline impulsively throws a reception to honor the happy couple, at which she gets drunk, but things turn serious when Julia's wealthy father's chauffeur arrives and summons her to talk - and for the first time in her life Julia turns down her father's money and announces she will stay married to the man she loves.

    Director:James Burrows
    Writer:Unknown

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  15. Caroline in the City Season 3 Episode 11 - Caroline and the Used Car Salesman
    7.3/10(51 votes)

    #15 - Caroline and the Used Car Salesman

    S3:E11

    Caroline becomes convinced that Richard is having an affair - but he is really moonlighting as a used car salesman to earn extra Christmas cash. Enter Del and Charlie in search of a used Porsche.

    Director:Unknown
    Writer:Unknown

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  16. Caroline in the City Season 4 Episode 9 - Caroline and the Booby Trap
    7.3/10(54 votes)

    #16 - Caroline and the Booby Trap

    S4:E9

    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.

    Director:Ted Wass
    Writer:Unknown

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  17. Caroline in the City Season 1 Episode 10 - Caroline and the Christmas Break
    7.2/10(75 votes)

    #17 - Caroline and the Christmas Break

    S1:E10

    Botched attempts to plan a holiday trip with Del lead Caroline to reconsider their relationship; Annie brews an elaborate scheme to help Richard break up with Shelly.

    Director:James Burrows
    Writer:Unknown

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  18. Caroline in the City Season 2 Episode 7 - Caroline and Victor/Victoria
    7.2/10(57 votes)

    #18 - Caroline and Victor/Victoria

    S2:E7

    Annie poses as a man to prepare for a ""Victor/Victoria"" audition.

    Director:Howard Deutch
    Writer:Bill Masters

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  19. Caroline in the City Season 3 Episode 9 - Caroline and the Bitter Beast
    7.2/10(58 votes)

    #19 - Caroline and the Bitter Beast

    S3:E9

    When Annie discovers an old musical notebook among the possessions Richard wants to store in Caroline's locker, teasing leads to genuine surprise when one of Richard's compositions turns out to be the tune to ""The Way We Were,"" which won a Grammy award for Richard's summer camp instructor, Marvin Hamlisch. With Annie pretending to be his legal counsel, Richard braves Hamlisch's ferociously protective housekeeper Olga and steals the trophy, then begins hostage negotiations. Meanwhile, Caroline encounters her former blind date Trevor and they resume a relationship, complicated by Trevor's German Shepherd who remains stubbornly loyal to Trevor's former girlfriend.

    Director:Shelley Jensen
    Writer:Oliver Goldstick

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  20. Caroline in the City Season 3 Episode 13 - Caroline and the Love That Dares Not Speak its Name (2)
    7.2/10(58 votes)

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

    S3:E13

    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.

    Director:James Burrows
    Writers:Brian Hargrove, Jack Kenny

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  21. Caroline in the City Season 3 Episode 26 - Caroline and the Bullfighter (2)
    7.2/10(51 votes)

    #21 - Caroline and the Bullfighter (2)

    S3:E26

    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

    Director:Michael Zinberg
    Writer:Unknown

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  22. Caroline in the City Season 1 Episode 6 - Caroline and the Folks
    7.1/10(82 votes)

    #22 - Caroline and the Folks

    S1:E6

    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.

    Director:James Burrows
    Writers:Marco Pennette, Fred Barron

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  23. Caroline in the City Season 1 Episode 19 - Caroline and the Movie
    7.1/10(74 votes)

    #23 - Caroline and the Movie

    S1:E19

    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.

    Director:Tom Cherones
    Writer:Bill Prady

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  24. Caroline in the City Season 2 Episode 12 - Caroline and the Perfect Record
    7.1/10(61 votes)

    #24 - Caroline and the Perfect Record

    S2:E12

    Caroline's romance is beached when Joe's ex returns from an environmental mission.

    Director:Michael Zinberg
    Writer:Unknown

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  25. Caroline in the City Season 2 Episode 18 - Caroline and the Monkeys
    7.1/10(57 votes)

    #25 - Caroline and the Monkeys

    S2:E18

    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.

    Director:Andrew Tsao
    Writer:Donald Todd

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Best Episodes Summary

"Caroline and the Ex-Wife" is the best rated episode of "Caroline in the City". It scored 8/10 based on 134 votes. Directed by Tom Cherones and written by Unknown, it aired on 3/28/1996. This episode scored 0.3 points higher than the second highest rated, "Caroline and the Wayward Husband (3)".