This 1995–99 NBC Sitcom was a starring vehicle for Lea Thompson, who played successful Manhattan comic strip artist Caroline Duffy. Wacky friends included grim Richard (colorist with pretensions of being a 'serious' artist), Cloudcuckoolander Charlie, slutty Annie (struggling actress and perpetual cast member of Cats), and dandy ex-boyfriend Del.
Contains examples of:
- A-Cup Angst: Annie exhibits this in the season 4 episode "Caroline and the Booby Trap".
- As Herself: Joanne Worley.
- Author Avatar: An in-universe example, with Caroline's life providing content for her eponymous comic strip.
- Back for the Finale: Charlie, after leaving the show early in the final season, made a return appearance in the final episode.
- Betty and Veronica: Caroline and Julia for Richard.
- Del and Richard for Caroline. Just don't tell angst-ridden Deadpan Snarker Richard he's Betty.
- Body Swap: In the Formula-Breaking Episode "Caroline and The Outer Limits''.
- Casting Gag: The Dick Van Dyke Show stars Rose Marie and Morey Amsterdam guest starred in "Caroline and the Watch" as an old married couple.
- Catchphrase: A shared one: when hearing something incredible Caroline would say, "Get Out!" and her friend Annie would rejoin, "I'm out!" (or vice versa).
- Celebrity Paradox: Caroline makes fun of Howard the Duck, a movie Lea Thompson starred in.
- Chuck Cunningham Syndrome: Remo, the owner of the restaurant which Caroline and friends frequented, appeared in the majority of episodes during the first two seasons but vanished without explanation midway through Season Three.
- Converting for Love: In "Caroline and the Nice Jewish Boy", Del dates a Jewish woman who apparently only dates Jewish men, so he lies and tells her he's Jewish so he can continue seeing her. He doesn't actually convert, but he does get a circumcision in order to maintain the ruse. Right as he's about to go into surgery, she dumps him for another man who isn't even Jewish, but by then it's too late for Del to back out.
- Crossover: One episode of Friends has Joey and Chandler meeting Caroline, who she mistakes for a gay couple. The very night that episode aired, Chandler appeared on the following episode of Caroline in the City.
- Crossover Punchline: The episode "Caroline and the Bad Back" ends with Niles and Daphne of Frasier discussing whether the most recent strip is funny.
- Cut Short: The final episode ends with Richard interrupting Caroline's wedding to Randy. We never find out which man she chooses.
- Dead Artists Are Better: Richard resigns himself to the fact that his talent won't be recognized until after he's dead. In "Caroline and the Dearly Departed", when he is reported dead due to a misunderstanding, he becomes quite gleeful at his newfound popularity.
- Deadpan Snarker: Richard, and to some extent, Annie.
- The Ditz: Charlie.
- Down on the Farm: Caroline's hometown is Peshtigo, Wisconsin and there are visits to said hometown, although it's more in a region where timber is the major industry, and there is no way a near-Yooper would have an even and controlled accent like Caroline's. (Thompson is from Rochester, Minnesota - on the other side of Wisconsin - and her natural accent does have a muted "Minnesota nice" affect to it.)
- Dying Declaration of Love: Subverted. A drugged-up and about to enter surgery Richard confesses to Caroline that he loves her. Caroline is shocked... until Richard says the same thing to the nurse moments later.
- Everyone Can See It: Even Del, Caroline's former fiance, thinks she and Richard are perfect for each other.
- Fake-Out Make-Out: Del and Richard, in order sell a piece of art from an all-gay gallery.
- Girl Next Door: Caroline is a bland garden variety.
- Goth: Despite being blond-haired and bespectacled, Richard dresses in all black and has the stereotypically morose personality.
- Handsome Lech: Del.
- Hooked Up Afterwards: Annie and Del get together in the last two episodes.
- Idiosyncratic Episode Naming: "Caroline and the _____ ".
- Imagine Spot: The plastic surgeon in "Caroline and the Booby Trap" shows Caroline how she would look with enhanced breasts, prompting one of these for Caroline. The Imagine Spot ends with Caroline having D-Cup Distress.
- Joisey: Annie is from Paramus; her mother is very much a caricature of the Italian Jersey housewife stereotype.
- Just Friends: Caroline and Richard.
- Locked in a Freezer: Inverted - Richard gets locked in the back room of a video rental store with its owner, an elderly Asian man. This is a problem since Richard was on his way to a romantic rendezvous with Caroline.
- Love Letter Lunacy: A major plot point at the end of Season One which continues to influence events in Season Two.
- Love Triangle: Caroline doesn't awaken to Richard's love for her until his ex-wife shows up, with Richard's surprise baby in tow.
- Mars and Venus Gender Contrast: Yet another female-oriented '90s sitcom with this view on relationships. One critic called CITC Sex and the City minus the sex.
- Mistaken for Gay: Richard; ironic because the actor who played him is actually gay.
- In another episode, an insurance agent believes Del and Charlie to be a gay couple; the two end up playing along with it because it will get them a better rate on their insurance.
- Ms. Fanservice: as a thank you for showing her old flame around New York Caroline promises Del she will wear a "certain little something" for him. This turns out to be skimpy black lingerie complete with Lolita style sunglasses and a cherry lollipop, the normally prim Caroline demonstrating her more seductive side.
- Naked People Are Funny: Caroline showing Richard her naked body for the first time... not realizing that Richard is not alone.
- In "Caroline and the Killer Dad," Del changes the punchline in Caroline's strip without telling her and then has to beg a succession of editors to allow him to change it back. The first one really likes his new leather jacket. The second really likes his shirt. At the end of the episode, Caroline admits that she now thinks his punchline was funnier ... oblivious to the fact that Del and Charlie are both standing behind her in the nude.
- Oblivious to Love: Caroline to Richard throughout the first 2 seasons, Richard to Caroline in the first half of season 3.
- Opposites Attract: Cheery girl-next-door Caroline and morbid, deadpan Richard
- Please Dump Me: Richard's attempts to get annoying clingy girlfriend Shelley to break up with him backfire spectacularly.
- Pyromaniac: One of Del's girlfriends turns out to be one of these. Then he makes the mistake of breaking up with her...
- Reading the Stage Directions Out Loud: When Caroline was reading Richards memorial speech (which he had written himself) at his fake funeralCaroline:”As the curtain descents, far to early on this brilliant career, we remember the artist, Richard Karinsky. Indicate my body.”(she realises her mistake) “…of work.”(she indicates his paintings)
- Really Gets Around: Annie.
- Revenge of the Nerd: Annie attempts this at a high school reunion and fails.
- Rich Bitch: Julia, Richard's ex.Julia: When you're Italian, you're always late. Capisce.
Annie: Hey. I'm Italian, and I'm always on time.
Julia: Really? I do not recall where New Jersey lies in the boot of Italy.
Annie: [glares] Let me get a boot, I'll show ya. - Romantic False Lead: Sofia Milos. Also, all of Caroline's boyfriends besides Richard.
- Sensitive Guy and Manly Man: Richard and Del
- Sequential Artist: Caroline.
- "Shaggy Dog" Story: Richard wins a contest where he gets to try to sink a basketball at a game. He's able to make the basket, but he's rendered ineligible for the prize when it's discovered that the newspaper that's sponsoring the event also runs Caroline's strip, making him an employee by extension.
- Sitcom Arch-Nemesis: Caroline's rivalry with the cartoonist of Cathy.
- Snark-to-Snark Combat: Most of Richard and Annie's interactions.
- Speak Now or Forever Hold Your Peace: the final episode, ends in a cliffhanger.
- Spicy Latina: Richard's Italian ex, Julia. Emphasis on spicy.
- Starving Artist: Richard
- Status Quo Game Show: Richard isn't allowed to keep $100,000 he wins in a contest because Caroline's strip is run in the paper sponsoring it.
- Stylistic Suck: Caroline's comic strip.
- Take That!: Baseketball was soundly mocked in the episode where Richard gets trapped in a video store. The owner anticipated it to be a huge hit and bought a mountain of copies.
- The Glasses Gotta Go: A rare male example. Richard always removes his glasses in scenes where he's a plausible love interest.
- Tiny Guy, Huge Girl: In one episode Dell got into a panic once he noticed that his new girlfriend was taller than him. He then desperately tried to keep her from noticing, Hilarity Ensues.
- Tomboy and Girly Girl: Caroline and Annie, respectively.
- Unrequited Love Switcheroo: Richard/Caroline/Julia.
- Will They or Won't They?: Caroline and Richard (torturously).
