No. 1
Notting Hill 1999
Her No. 1. Richard Curtis's follow-up to Four Weddings, with Julia Roberts playing a movie star who's engaging with her own fame.
The Big Picture · Top Five · Discussion · Interview
Top Five Movies of 1999, Plus David Modigliani on ‘Running With Beto’ | Discussion
March 26, 2019/ 106 min/ Sean Fennessey · Amanda Dobbins · Chris Ryan
Sean Fennessey, Amanda Dobbins, and Chris Ryan each draft a top five from 1999, a year they argue produced more great movies than any other, alongside a run of forgettable ones from great directors. Then Sean talks to documentarian David Modigliani about 'Running With Beto.'
22 films across 5 segments.
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.
Amanda's Top Fivemovies of 1999, best to worst
No. 2
The Talented Mr. Ripley 1999
Damon's best performance, she says, an ability he's since edited out of his acting except in flashes as Linus in the Ocean's movies.
No. 3
10 Things I Hate About You 1999
The most rewatchable of the year's teen movies, carried by Heath Ledger's breakout.
No. 5
The Thomas Crown Affair 1999
Her actual favorite movie of the five, just not her No. 1: the McTiernan remake with Pierce Brosnan and Rene Russo.
Chris's Top Fivemovies of 1999, best to worst
No. 1
Fight Club 1999
Filmmaking at its best across the board, though he thinks the way people talk about it has outlasted the movie itself.
No. 3
The Insider 1999
Michael Mann's only non-action movie: Pacino and Crowe on the Brown & Williamson tobacco story.
No. 4
The Blair Witch Project 1999
The defining theater experience of his life; he remembers most of the opening-weekend crowd walking out convinced it was real.
No. 5
Go 1999
A rave-culture redo of Pulp Fiction he thinks has aged into a better L.A. time capsule than Swingers.
Sean's Top Fivemovies of 1999, best to worst
No. 1
Fight Club 1999
Says more about 2019 than about 1999, he thinks, maybe because of what got made of it.
No. 2
Magnolia 1999
PTA pouring every feeling he had into the longest movie he could make, right after Boogie Nights got him called the next Scorsese.
No. 3
Three Kings 1999
A heist movie about Gulf War soldiers who arrived too late for their war, shot during a production notorious for Clooney and David O. Russell coming to blows.
No. 4
South Park: Bigger, Longer & Uncut 1999
A movie musical with the safety off, its songs sung by everyone from Satan to Saddam Hussein.
No. 5
The Matrix 1999
The first time since seeing Star Wars that he remembers a movie hitting him that hard in a theater.
Eyes Wide Shutoff everyone's list, but not off the table
Eyes Wide Shut 1999
Amanda calls it a fascinating case study of Tom Cruise and Nicole Kidman's actual marriage; Sean ranks it low among great Kubrick films but still says it's the real thing.
In conversation
David Modigliani on
Running with Beto 2019
His HBO documentary on Beto O'Rourke's 2018 Senate run, built around whether he could revive Texas turnout rather than whether he'd win.
David Modigliani on
Street Fight 2005
Marshall Curry's film on Cory Booker's first, losing mayoral run. One of two campaign docs he had his crew watch to prove a loss can still make a great film.
David Modigliani on
Mitt 2014
The other reference point: Romney's failed 2012 campaign, which he says felt non-partisan even to viewers who didn't share Romney's politics.
David Modigliani on
The War Room 1993
D.A. Pennebaker's Clinton-campaign doc, cited for its focus on staffers rather than the candidate.
David Modigliani on
Crisis: Behind a Presidential Commitment 1963
A friend's recommendation after the fact: JFK and Bobby Kennedy navigating George Wallace's schoolhouse-door standoff.
David Modigliani on
Don't Look Back 1967
Pennebaker's Dylan tour film, his biggest single influence on Running with Beto for its fly-on-the-wall intimacy.
Also mentioned raised along the way
Also 1999, in passing Happy, TexasAt First SightAmerican BeautyOffice SpaceThe Green MileGirl, InterruptedThe HurricaneStar Wars: Episode I - The Phantom MenaceToy Story 2American PieAustin Powers: The Spy Who Shagged MeThe MummyThe World Is Not EnoughPokémon: The First MovieThe Sixth SenseBringing Out the DeadSummer of SamMusic of the HeartTrue CrimeSleepy HollowGloriaThe MuseThe Straight StoryRandom HeartsMumfordCruel IntentionsShe's All ThatNever Been KissedVarsity BluesJawbreakerAny Given SundayFor Love of the GameMystery, AlaskaBig DaddyDeep Blue SeaLake PlacidRun Lola RunAll About My Mother
Not films filtered out: TV, games, ads
TV Game of ThronesDawson's CreekSouth Park (TV series)The Daily ShowBig Little Lies