The Thomas Crown Affair (1999)

The remake of the 1968 film starring Steve McQueen and Faye Dunaway is better. Insurance investigator Rene Russo pursues Pierce Brosnan (who steals priceless paintings), and they make a cool, sexy couple with real chemistry in a movie for grown-ups.

d: John McTiernan | imdb.com | trailer | Closed for cleaning.

Office Space (1999)

Mike Judge’s second film isn’t just a smart satire of the cubicle culture, capturing the zeitgeist of early 2000s downsizing. It is an anthem for anyone who has ever hated their job — with a gangsta rap soundtrack and the mafia-style execution of a printer.

d: Mike Judge | imdb.com | trailer

The Big Lebowski (1998)

Jeff Bridges casually plays the Dude, a man for whom casualness is a way of life — Creedence, White Russians and bowling with his buddies. Meanwhile, the Coen Brothers construct one hell of a ride — mistaken identity, kidnapping and Technicolor blackouts.

d: Coen Brothers | imdb.com | trailer | They peed on your rug.
Blow on my toes. | Jesus | The Bag Man | Shomer Shabbos

Cop Land (1997)

Sylvester Stallone gained weight to play the oafish sheriff of a New York suburb, but the details are in his hang-dog face and weary eyes. The film evolves into a Western morality tale, brilliantly supported by Harvey Keitel, Ray Liotta and Robert De Niro.

d: James Mangold | imdb.com | trailer | “Charlie Rose”

Get Shorty (1995)

Director Barry Sonnenfeld’s smart, hip adaptation of Elmore Leonard’s novel zooms along, lampooning the movie business with periodic punches to the face. John Travolta is the ultra-cool Chili Palmer, a Miami mobster who wants to be a Hollywood producer.

d: Barry Sonnenfeld | imdb.com | trailer | I’m Ray Barboni.

Kicking and Screaming (1995)

The year after college is the hardest for four friends who end up hanging out around school and talking about nothing. Chris Eigeman, Parker Posey and Eric Stoltz (as the career student) steal a wonderfully funny movie about not growing up.

d: Noah Baumbach | imdb.com | trailer | Life after college