Name: Jack & Jill
Genre: Comedy, Drama
Released: 1999-09-26
Rating: 7.6
Cast: Ivan Sergei, Amanda Peet, Justin Kirk, Sarah Paulson, Jaime Pressly

Amanda Peet and Ivan Sergei play will-they-won't-they before it was exhausting — peak '99 NYC energy.

pre-millennial anxietySex and the City for normiescoffee shop philosophy

Latest Episode

43 min

Season 2 • Episode 13

Latest

... And Jack & Jill Came Down the Hill (2)

Apr 11, 2001

Jack and Jill scramble to keep their wedding on track after the hurricane destroys their Bahamas plan, but the couple is in a bad place.

Overview

Comedy Drama

A lighthearted romantic comedy about post-collegiate life, love and career in New York City.

Content warning

new york city dating group of friends young adult relationship twenty something college graduate

quarter-life limbocareer vs. connectionchosen family dynamicsthe myth of 'having it figured out'

Standout Aspects

Acting

Amanda Peet's chaotic magnetism carries every scene.

Writing

Randi Mayem Singer's razor dialogue before Mad About You fame.

Costume

Tank tops over long sleeves. It was a disease.

Best for:Solo·Rewatch

Creator

Randi Mayem Singer

First AiredSep 26, 1999

StatusEnded

Vibe

Pacesteady

Intensitylow

Tonelight

Feellight

Seasons2·Episodes32

Top Cast

Ivan Sergei

David 'Jill' Jillefsky

Amanda Peet

Jacqueline 'Jack' Barrett

Justin Kirk

Bartolomew 'Barto' Zane

Sarah Paulson

Elisa Cronkite

Jaime Pressly

Audrey Griffin

Simon Rex

Michael 'Mikey' Russo

Ask about Jack & Jill

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Deep Dive

Trivia, insights & behind the scenes

Trivia

Randi Mayem Singer later wrote Mrs. Doubtfire and created The Crazy Ones — this was her first showrunning gig.

Cultural

The WB cancelled it after two seasons for Dawson's Creek ratings dominance, making it a forgotten stepping stone between Felicity and the rom-com boom.

Gallery