The Best Episodes of Caroline in the City Season 1

Episode Rankings

1. #1 Fan Favorite
   

   7.5/10(101 votes)

   #1 - Caroline in the City

   S1:E19/21/1995

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

   Director:James Burrows

   Writers:Marco Pennette, Fred Barron, Dottie Dartland Zicklin

   Be the first to start the conversation for this episode

   Director:James Burrows

   Writers:Marco Pennette, Fred Barron, Dottie Dartland Zicklin
2. 

   7.0/10(77 votes)

   #2 - Caroline and the Mugger

   S1:E29/28/1995

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

   Director:James Burrows

   Writer:Unknown

   Be the first to start the conversation for this episode

   Director:James Burrows

   Writer:Unknown
3. 

   7.3/10(71 votes)

   #3 - Caroline and the Gay Art Show

   S1:E310/5/1995

   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.

   Director:James Burrows

   Writer:Unknown

   Be the first to start the conversation for this episode

   Director:James Burrows

   Writer:Unknown
4. 

   6.8/10(70 votes)

   #4 - Caroline and the Bad Back

   S1:E410/12/1995

   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.

   Director:James Burrows

   Writer:Bill Prady

   Be the first to start the conversation for this episode

   Director:James Burrows

   Writer:Bill Prady
5. 

   7.0/10(72 votes)

   #5 - Caroline and the ATM

   S1:E510/19/1995

   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.

   Director:Rod Daniel

   Writer:Mark Wilding

   Be the first to start the conversation for this episode

   Director:Rod Daniel

   Writer:Mark Wilding
6. 

   7.1/10(82 votes)

   #6 - Caroline and the Folks

   S1:E611/2/1995

   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.

   Director:James Burrows

   Writers:Marco Pennette, Fred Barron

   Be the first to start the conversation for this episode

   Director:James Burrows

   Writers:Marco Pennette, Fred Barron
TRENDING NOW
The 20 BEST Episodes of Caroline in the City
READ
7. 

   7.0/10(68 votes)

   #7 - Caroline and the Opera

   S1:E711/9/1995

   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.

   Director:Tom Cherones

   Writers:Marco Pennette, Fred Barron

   Be the first to start the conversation for this episode

   Director:Tom Cherones

   Writers:Marco Pennette, Fred Barron
8. 

   7.0/10(67 votes)

   #8 - Caroline and the Balloon

   S1:E811/16/1995

   Caroline is blown away by an opportunity to march in the Thanksgiving Day Parade - something she had dreamed of since high school mononucleosis kept her out of her marching band - when the giant balloon of her character Caroline escapes, injures parade marshal Florence Henderson, and threatens Staten Island.

   Director:Tom Cherones

   Writer:Bill Prady

   Be the first to start the conversation for this episode

   Director:Tom Cherones

   Writer:Bill Prady
9. 

   6.9/10(64 votes)

   #9 - Caroline and the Convict

   S1:E912/7/1995

   Annie is really in love with her new boyfriend, a recent ex-con who did time for breaking and entering - and who is the obvious suspect when Caroline's apartment is burgled. Richard is upset because one of the stolen items was his painting of his mother's womb.

   Director:Rod Daniel

   Writer:Rob Lotterstein

   Be the first to start the conversation for this episode

   Director:Rod Daniel

   Writer:Rob Lotterstein
10. 

    7.2/10(75 votes)

    #10 - Caroline and the Christmas Break

    S1:E1012/14/1995

    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

    Be the first to start the conversation for this episode

    Director:James Burrows

    Writer:Unknown
11. 

    7.5/10(65 votes)

    #11 - Caroline and the Gift

    S1:E111/4/1996

    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

    Be the first to start the conversation for this episode

    Director:James Burrows

    Writer:Bill Prady
12. 

    7.0/10(62 votes)

    #12 - Caroline and the Married Man

    S1:E121/11/1996

    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.

    Director:Tom Cherones

    Writer:Wil Calhoun

    Be the first to start the conversation for this episode

    Director:Tom Cherones

    Writer:Wil Calhoun
13. 

    6.7/10(62 votes)

    #13 - 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

    Be the first to start the conversation for this episode

    Director:Tom Cherones

    Writer:Unknown
14. 

    7.4/10(70 votes)

    #14 - Caroline and the Watch

    S1:E142/1/1996

    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

    Be the first to start the conversation for this episode

    Director:James Burrows

    Writer:Mark Wilding
15. 

    6.9/10(63 votes)

    #15 - Caroline and the Bad Date

    S1:E152/15/1996

    Del asks Richard to join him on a double date with two gorgeous models; Caroline meets a man buying a sweater, but he turns out to be a paranoid bore.

    Director:Tom Cherones

    Writer:Bill Prady

    Be the first to start the conversation for this episode

    Director:Tom Cherones

    Writer:Bill Prady
16. 

    7.5/10(66 votes)

    #16 - Caroline and the Proposal

    S1:E162/22/1996

    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.

    Director:James Burrows

    Writers:Marco Pennette, Fred Barron

    Be the first to start the conversation for this episode

    Director:James Burrows

    Writers:Marco Pennette, Fred Barron
17. 

    7.0/10(59 votes)

    #17 - Caroline and the Kid

    S1:E173/14/1996

    Ultra-competitive Del has feelings of inadequacy after meeting Caroline's debonair ex-boyfriend Marco, especially when the towels come off at the gym; Caroline and Richard are hired to paint a mural for the bedroom of Martin Lapper, a demonic spoiled rich kid.

    Director:Tom Cherones

    Writers:Bill Masters, Wil Calhoun

    Be the first to start the conversation for this episode

    Director:Tom Cherones

    Writers:Bill Masters, Wil Calhoun
18. 

    8.0/10(134 votes)

    #18 - Caroline and the Ex-Wife

    S1:E183/28/1996

    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.

    Director:Tom Cherones

    Writer:Unknown

    Be the first to start the conversation for this episode

    Director:Tom Cherones

    Writer:Unknown
19. 

    7.1/10(74 votes)

    #19 - Caroline and the Movie

    S1:E194/4/1996

    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.

    Director:Tom Cherones

    Writer:Bill Prady

    Be the first to start the conversation for this episode

    Director:Tom Cherones

    Writer:Bill Prady
20. 

    6.8/10(84 votes)

    #20 - Caroline and the Cereal

    S1:E204/18/1996

    Caroline's agent (Taylor) likes the idea of featuring her comic-strip character on a cereal box, but the artist flakes out after a closer look at the product, which she feels has an unfortunate resemblance to a certain part of the female anatomy. A chaotic focus group sessions does little to allay her misgivings.

    Director:Pamela Fryman

    Writer:Unknown

    Be the first to start the conversation for this episode

    Director:Pamela Fryman

    Writer:Unknown
21. 

    6.8/10(61 votes)

    #21 - 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

    Be the first to start the conversation for this episode

    Director:James Burrows

    Writers:Dottie Dartland Zicklin, Charles Harper Yates
22. 

    6.8/10(59 votes)

    #22 - Caroline and the Bridesmaids

    S1:E225/9/1996

    Preparations for the wedding cause friction between Caroline and Annie, who can't seem to take her responsibilities as maid of honor seriously.

    Director:Tom Cherones

    Writers:Bill Masters, Wil Calhoun

    Be the first to start the conversation for this episode

    Director:Tom Cherones

    Writers:Bill Masters, Wil Calhoun
23. 

    7.5/10(65 votes)

    #23 - Caroline and the Wedding

    S1:E235/16/1996

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

    Director:James Burrows

    Writer:Bill Masters

    Be the first to start the conversation for this episode

    Director:James Burrows

    Writer:Bill Masters
24. 

    6.4/10(58 votes)

    #24 - 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

    Be the first to start the conversation for this episode

    Director:James Burrows

    Writers:Marco Pennette, Fred Barron