The Worst Episodes of Caroline in the City

Episode Rankings

1. #1 Worst Episode
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   5.8/10(46 votes)

   #1 - Caroline and the Bar Mitzvah

   S4:E1012/14/1998

   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.

   Director:Unknown

   Writer:Unknown

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   Director:Unknown

   Writer:Unknown
2. 

   6.0/10(41 votes)

   #2 - Caroline and the Big Move

   S4:E224/26/1999

   As Caroline and Richard prepare to leave for Italy to visit his newborn son, Richard makes a confession that gives Caroline second thoughts about their future together: he never wanted to have children. But when he arrives alone in Italy, Richard discovers that Julia has abandoned the baby, and slowly becomes a model father. Meanwhile, Annie and Del begin a clandestine relationship. Flashing forward six months later, the series finale finds Caroline headed to the altar with Randy, when an unexpected guest arrives during the wedding ceremony: Richard, holding his infant son...

   Director:Ted Wass

   Writer:Marco Pennette

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   Director:Ted Wass

   Writer:Marco Pennette
3. 

   6.1/10(35 votes)

   #3 - Caroline and the 2000th Strip

   S4:E173/8/1999

   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.

   Director:Unknown

   Writer:Unknown

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   Director:Unknown

   Writer:Unknown
4. 

   6.2/10(41 votes)

   #4 - Caroline and the Rotten Plum

   S4:E310/5/1998

   Caroline settles into her new workplace, where she inadvertently - and immediately - ticks off office manager Plum, who banishes Caroline and Richard to the basement. Meanwhile, Annie lusts after her yoga teacher Jonathan, but learns from Angie that he is a former porn performer.

   Director:Ted Wass

   Writer:Oliver Goldstick

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   Director:Ted Wass

   Writer:Oliver Goldstick
5. 

   6.2/10(42 votes)

   #5 - Caroline and the Horny Kid

   S4:E131/18/1999

   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.

   Director:Ted Wass

   Writer:Tom Burkhard

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   Director:Ted Wass

   Writer:Tom Burkhard
6. 

   6.2/10(43 votes)

   #6 - Caroline and the Ancestral Home

   S4:E163/15/1999

   Caroline and the gang visit her family's home in Wisconsin and learn her parents are selling the house. Distraught, she prolongs her stay (while Richard unwillingly bonds with the locals), and ultimately decides to preserve her childhood memories by buying the house herself.

   Director:Ted Wass

   Writer:Unknown

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   Director:Ted Wass

   Writer:Unknown
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7. 

   6.2/10(38 votes)

   #7 - Caroline and the Sudsy Guy

   S4:E183/22/1999

   Caroline's plans to rent out her house in Wisconsin hit an unexpected snag when Grandma Duffy refuses to leave, forcing Caroline to return to Wisconsin, where she is surprised to learn that her former boyfriend Randy will be her new tenant. Meanwhile, Richard has his hands full in New York when he agrees to take Caroline's place by caring for Annie (who is sick) and Del (who thinks his girlfriend may be cheating on him).

   Director:Ted Wass

   Writer:Tom Burkhard

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   Director:Ted Wass

   Writer:Tom Burkhard
8. 

   6.3/10(38 votes)

   #8 - Caroline and Joanie and the Stick

   S4:E153/8/1999

   Caroline tries to right an old wrong by giving up a romantic weekend in Boston with Richard to help out a visiting childhood chum, Joanie, whom Caroline once bullied in school. Meanwhile, a lonely Annie finds unexpected companionship with a smooth-talking parrot when she agrees to bird-sit for Dave, and Del has trouble accepting the fact that his new girlfriend Lisa is taller than he is.

   Director:Ted Wass

   Writer:Unknown

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   Director:Ted Wass

   Writer:Unknown
9. 

   6.4/10(41 votes)

   #9 - Caroline and the Office

   S4:E29/28/1998

   When Carol can no longer stand the pressure Del is putting on her to work out of her new corporate office instead of her home, a reluctant Caroline discovers that Richard has been sleeping there: his vengeful father-in-law has stripped him of apartments, possessions and credit cards, and Charley has been using Richard's old apartment as a makeshift hotel for visiting Russians. Then Richard falls afoul of the militaristic office manager Plum, who subjects him to standard employment tests, including a visit to the staff psychologist - who finds Richard's behavior a little odd.

   Director:Ted Wass

   Writers:Gary Murphy, Neil Thompson

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   Director:Ted Wass

   Writers:Gary Murphy, Neil Thompson
10. 

    6.4/10(40 votes)

    #10 - Caroline and the Fright Before Christmas

    S4:E1112/21/1998

    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.

    Director:Ted Wass

    Writer:Oliver Goldstick

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    Director:Ted Wass

    Writer:Oliver Goldstick
11. 

    6.5/10(52 votes)

    #11 - Caroline and the Guy Who Gets There Too Soon

    S2:E410/22/1996

    Realizing Caroline never received his love letter, Richard labors to retrieve it from her friend's apartment.

    Director:Gordon Hunt

    Writer:Donald Todd

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    Director:Gordon Hunt

    Writer:Donald Todd
12. 

    6.5/10(49 votes)

    #12 - Caroline and the New Neighbor

    S2:E204/8/1997

    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.

    Director:Michael Zinberg

    Writer:Unknown

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    Director:Michael Zinberg

    Writer:Unknown
13. 

    6.6/10(49 votes)

    #13 - Caroline and the Condom

    S1:E248/5/1996

    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.

    Director:James Burrows

    Writers:Marco Pennette, Fred Barron

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    Director:James Burrows

    Writers:Marco Pennette, Fred Barron
14. 

    6.6/10(43 votes)

    #14 - Caroline and the Getaway

    S2:E172/25/1997

    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.

    Director:James Burrows

    Writer:Unknown

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    Director:James Burrows

    Writer:Unknown
15. 

    6.6/10(42 votes)

    #15 - Caroline and the Cabbie

    S3:E183/9/1998

    Richard gets a chance to have a painting exhibited at the New York Public Library, but falls victim to on-line addiction at a cyber cafe. An outraged Caroline files a complaint against a rude cabbie, but Richard is her only witness (""A rude cab driver in New York? What's next, tall buildings?"") and fails to show up at the hearing. Meanwhile, after literal years on the waiting list, Annie finally gets an appointment with famous hair stylist Olaf, only to have Del and Charlie invade her session with a ridiculous scheme to market the hair sweepings of the famous - which Olaf loves.

    Director:Will Mackenzie

    Writer:Nancy Steen

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    Director:Will Mackenzie

    Writer:Nancy Steen
16. 

    6.6/10(36 votes)

    #16 - Caroline and the Marriage Counselor (2)

    S3:E245/4/1998

    Julia and Richard's marriage counselor starts work as Richard's replacement but finds that everyone still wants him to give them relationship advice.

    Director:Shelley Jensen

    Writer:Oliver Goldstick

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    Director:Shelley Jensen

    Writer:Oliver Goldstick
17. 

    6.6/10(38 votes)

    #17 - Caroline and the Drycleaner

    S4:E410/12/1998

    It's just not Annie's day: she gets fired from Cats after eight years and is immediately dumped by her agent. To get back some self esteem, she agrees to go out with her dry cleaner to his dry cleaners' annual banquet, but when she attempts to strut both their stuff on the dance floor, she succeeds only in fracturing his leg. Meanwhile, since sales of her greeting cards are down, Del talks Caroline into attending a focus group which some wild new ideas about Caroline's cartoon strip. Richard is aghast to find Caroline seriously considering some of them (turning Salty into a dog, giving Caroline super-powers); then Del announces that all greeting card sales are down, Caroline's less than most.

    Director:Ted Wass

    Writer:Unknown

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    Director:Ted Wass

    Writer:Unknown
18. 

    6.7/10(40 votes)

    #18 - Caroline and the Egg

    S3:E611/3/1997

    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.

    Director:Arlene Sanford

    Writer:Nancy Steen

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    Director:Arlene Sanford

    Writer:Nancy Steen
19. 

    6.7/10(42 votes)

    #19 - Caroline and the Little White Lies

    S3:E204/6/1998

    For insurance purposes, Del and Charlie pretend to be gay, but then Del meets a beautiful woman at a party, and in trying to pursue her gets himself and Charlie invited to be the couple of honor at a gay pride rally. Meanwhle, Richard reluctantly agrees to change his appearance so that he'll be picked for jury duty, and Annie lies to her mom about her dad's fiancée.

    Director:Ted Wass

    Writer:Nancy Steen

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    Director:Ted Wass

    Writer:Nancy Steen
20. 

    6.7/10(39 votes)

    #20 - Caroline and the Marriage Counselor (1)

    S3:E235/4/1998

    Caroline returns home to find Richard, Julia, Trevor, Annie, Del and Charlie bound and gagged together - which turns out to be the doing of a deranged marriage counselor, as we learn in a series of flashbacks: To quit or not to quit? That is the question Richard faces in this hour-long episode. When Julia is finally able to claim her inheritance, the Karinskys move into a penthouse and ponder leaving their jobs. While Mrs. Karinsky gives up bartending in a flash, Richard makes excuses about abruptly leaving Caroline. A concerned Julia hires a marriage counselor, who turns out to be more interested in Richard's job than his life. Meanwhile, Caroline suggests that she and Trevor move in together. Garry Shandling has a cameo as one of the therapist's other patients.

    Director:Shelley Jensen

    Writer:Oliver Goldstick

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    Director:Shelley Jensen

    Writer:Oliver Goldstick
21. 

    6.7/10(45 votes)

    #21 - Caroline and the Big Night

    S4:E711/9/1998

    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...

    Director:Howard Deutch

    Writer:Tom Burkhard

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    Director:Howard Deutch

    Writer:Tom Burkhard
22. 

    6.7/10(39 votes)

    #22 - Caroline and the Big Bad Bed

    S4:E121/11/1999

    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.""

    Director:Ted Wass

    Writers:Gary Murphy, Neil Thompson

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    Director:Ted Wass

    Writers:Gary Murphy, Neil Thompson
23. 

    6.7/10(40 votes)

    #23 - Caroline and the Firing Squad

    S4:E141/25/1999

    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.

    Director:Shelley Jensen

    Writer:Unknown

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    Director:Shelley Jensen

    Writer:Unknown
24. 

    6.8/10(54 votes)

    #24 - Caroline and the Twenty-Eight-Pound Walleye

    S1:E131/25/1996

    Caroline's parents (Holliman & Hartley) roll out the red carpet when she visits her home town for a ceremony in her honor, but something smells fishy when her brother (who has upstaged her all their lives) arrives with big news of his own.

    Director:Tom Cherones

    Writer:Unknown

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    Director:Tom Cherones

    Writer:Unknown
25. 

    6.8/10(53 votes)

    #25 - Caroline and Richard's Mom

    S1:E214/25/1996

    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.

    Director:James Burrows

    Writers:Dottie Dartland Zicklin, Charles Harper Yates

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    Director:James Burrows

    Writers:Dottie Dartland Zicklin, Charles Harper Yates