Oscar Nominee
The Talented Mr. Ripley 1999
The No. 1 overall pick. Minghella's Italy, young Damon, Jude Law, Gwyneth, Blanchett and Philip Seymour Hoffman all in flight.
The Big Picture · Draft
The 1999 Movie Draft
April 16, 2024/ 152 min/ Sean Fennessey · Amanda Dobbins · Chris Ryan · Van Lathan · Mallory Rubin · Joanna Robinson · Rob Mahoney
A seven-person snake draft of the movies of 1999, the 40th Big Picture draft, with each drafter filling a six-slot roster across Drama, Comedy, Action/Thriller/Horror, Blockbuster, Oscar Nominee, and Wild Card.
42 films across 1 segment.
AI-generated This episode was transcribed and analyzed with AI models. The matches aren't perfect — expect the occasional misheard title or a link to the wrong film.
The teams drafting the movies of 1999
Amanda Dobbins
Action / Thriller / Horror
The Thomas Crown Affair 1999
McTiernan's heist remake; Brosnan's best not-Bond, Rene Russo's clothes. She won't part with it for $10 million.
Blockbuster
Austin Powers: The Spy Who Shagged Me 1999
Taken partly out of spite. Heather Graham as Felicity Shagwell.
Comedy
Dick 1999
Kirsten Dunst and Michelle Williams as the girls behind Deep Throat; Will Ferrell's Bob Woodward.
Wild Card
The Best Man 1999
A melodramatic college-reunion movie with a stacked cast; a functional Regina Hall debut.
Rob Mahoney
Blockbuster
The Matrix 1999
Second overall. Plays like a noir for the first 40 minutes, then turns into an exposition dump, then becomes the superhero story of the era.
Comedy
Notting Hill 1999
Snatched from Amanda one pick early. Richard Curtis; Julia Roberts with a little edge.
Action / Thriller / Horror
eXistenZ 1999
The goopy-port other side of Jude Law; a Cronenberg double feature with The Matrix.
Drama
The Straight Story 1999
Lynch, presented by Disney; Richard Farnsworth nominated. Hits hardest if you're a brother of a brother.
Wild Card
Perfect Blue 1997
Satoshi Kon's pop-idol nightmare; maybe the scariest movie of the year, and pertinent to stan culture.
Van Lathan
Action / Thriller / Horror
Fight Club 1999
Van's favorite of the year. A sticky movie: late capitalism, confronting your delusions, peak Pitt.
Blockbuster
Star Wars: Episode I - The Phantom Menace 1999
Cost Van $200 (tires for a ride to Monroe). Terrible on exit, redeemed by the final lightsaber duel.
Oscar Nominee
American Beauty 1999
The Best Picture winner nobody else would touch. Van reads it as suburban satire; the table argues it takes itself too seriously.
Drama
Arlington Road 1999
A taut, very pre-9/11 paranoia thriller. Tim Robbins sinister, the good guys lose.
Wild Card
Dogma 1999
The Kevin Smith movie Van feels most connected to, a 'fuck your parents' film. Still hard to stream over rights.
Sean Fennessey
Blockbuster
The Sixth Sense 1999
Shyamalan; a Daily Show correspondent spoiled it for Sean, but it still worked. He watched it three times over the weekend.
Action / Thriller / Horror
Eyes Wide Shut 1999
Sean's most-anticipated of '99. Kubrick's last, released after his death; read about it in the Post at his warehouse job.
Comedy
South Park: Bigger, Longer & Uncut 1999
The movie playing when Sean's now-wife knew he was the one. 80 minutes, still relevant.
Drama
The Limey 1999
Soderbergh; Terence Stamp as a career criminal in L.A. Famous for the Soderbergh/Lem Dobbs argument commentary.
Oscar Nominee
Being John Malkovich 1999
Jonze and Kaufman; a gateway to weird mainstream movies, and to Lost in Translation.
Wild Card
Run Lola Run 1998
Tykwer; Franka Potente running, choose-your-own-adventure structure, all German techno. Bled into Bourne.
Joanna Robinson
Blockbuster
The Mummy 1999
A '99 banger that's only grown; the movie that made Brendan Fraser and a bisexual awakening for many.
Oscar Nominee
Magnolia 1999
PTA; Joanna's favorite Hoffman and Julianne Moore performances, and a huge Cruise moment. The double-VHS box set.
Action / Thriller / Horror
Galaxy Quest 1999
The Star Trek parody that hit on VHS and DVD. Weaver, Rickman, Rockwell, Shalhoub.
Comedy
Drop Dead Gorgeous 1999
Dry-as-a-bone beauty-pageant mockumentary. Dunst, Denise Richards, Kirstie Alley, Ellen Barkin. Not on streaming.
Mallory Rubin
Comedy
Office Space 1999
A patron-saint film of The Ringer; a heavily-worn DVD and a meme generator ever since.
Blockbuster
Toy Story 2 1999
A Pixar behemoth (and the table's agreed weakest Toy Story). 'When She Loved Me' will wreck you.
Action / Thriller / Horror
Lock, Stock and Two Smoking Barrels 1998
Guy Ritchie; Mallory watched it endlessly with a high-school boyfriend. Taken to Chris's dismay.
Wild Card
10 Things I Hate About You 1999
A top-10 movie of the year for her, grabbed early in Wild Card to keep it off the board. 'Can't Take My Eyes Off You.'
Drama
Princess Mononoke 1997
Miyazaki; beautiful and dark, still holds up. It was this or Iron Giant.
Oscar Nominee
The End of the Affair 1999
A Ralph Fiennes passion pick over any actual Oscar winner. Julianne Moore, and a cinematography nom.
Chris Ryan
Blockbuster
The Blair Witch Project 1999
One of the most memorable times Chris ever had in a theater; kicked off viral marketing. Van hated it in the theater.
Oscar Nominee
The Insider 1999
Michael Mann; Pacino's late-'90s Renaissance and Crowe slingshotting to best-movie-star-alive.
Comedy
Go 1999
Chris's Magnolia at the time. Katie Holmes, Sarah Polley, Timothy Olyphant. Overdue for a new scan.
Drama
Any Given Sunday 1999
Stone's football movie; Pacino's halftime speech, a Greek conception of drama.
Action / Thriller / Horror
8mm 1999
The Machine. Cage and Joaquin Phoenix; a sexually depraved blockbuster and the highest-rated Rewatchables ever.
Wild Card
Bowfinger 1999
One of Chris's favorite Steve Martin performances and a great Hollywood send-up. Poorly marketed at the time.
On the board, undrafted honorable mentions
American PieShe's All ThatNever Been KissedThe WoodEDtvSummer of SamBringing Out the Dead200 CigarettesAnalyze ThisThe Deep End of the OceanBaby GeniusesLake PlacidBatsThe World Is Not EnoughAll About My MotherTopsy-TurvySweet and LowdownCradle Will RockTitusBut I'm a CheerleaderTrue CrimeCookie's FortuneRatcatcherMystery, AlaskaOutside ProvidenceAmerican MovieJawbreakerSleepy HollowOctober SkyDeuce Bigalow: Male GigoloPaybackAnywhere but HereMan on the MoonBuena Vista Social ClubBeyond the MatDetroit Rock CityDouble JeopardyDrive Me CrazyEntrapmentBoys Don't CryGirl, InterruptedThe HurricaneThe Green MileThe Cider House RulesThe Virgin SuicidesStir of EchoesStigmataTeaching Mrs. TingleRavenousEnd of DaysDeep Blue SeaA Walk on the MoonRandom HeartsFor Love of the Game
Also mentioned raised along the way
Mentioned in passing Michael ClaytonSeabiscuitWar HorseMementoThe Bourne IdentityEternal Sunshine of the Spotless MindWitnessClerksChasing AmyJay and Silent Bob Strike BackThe Truman ShowNational TreasureInfernal AffairsJim & Andy: The Great BeyondThe Boy and the Heron
Not films filtered out: TV, games, ads
TV RipleyDawson's CreekSix Feet UnderTrue BloodBlue Eye SamuraiBlueyShōgunThe Daily Show
Podcasts Stick the LandingThe Rewatchables
Games FIFA World Cup Launch EditionCinematrix
Ads TremfyaBoar's HeadFanDuelNetflix FIFA World Cup