Hollywood on Hollywood

The Industry Looking in the Mirror

Los Angeles has always made films about itself — sometimes flattering, sometimes damning, always fascinating. These are the best films about the machinery of movies and fame.

Political
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Movies
7
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Created: October 26, 2026

The Collection

Sunset Boulevard

Sunset Boulevard

1950
1
Sunset Boulevard
1950
1
Sunset Boulevard
IMDb 8.4 / 10
Director Billy Wilder
Cast William Holden, Gloria Swanson, Erich von Stroheim
Box Office $299,645
Why An essential entry — Sunset Boulevard embodies exactly what this collection is about.
Mulholland Drive

Mulholland Drive

2001
2
Mulholland Drive
2001
2
Mulholland Drive
IMDb 7.9 / 10
Director David Lynch
Cast Naomi Watts, Laura Harring, Justin Theroux
Box Office $7,220,243
Why An essential entry — Mulholland Drive embodies exactly what this collection is about.
The Player

The Player

1992
3
The Player
1992
3
The Player
IMDb 7.5 / 10
Director Robert Altman
Cast Tim Robbins, Greta Scacchi, Fred Ward
Box Office $21,706,101
Why An essential entry — The Player embodies exactly what this collection is about.
Barton Fink

Barton Fink

1991
4
Barton Fink
1991
4
Barton Fink
IMDb 7.6 / 10
Director Joel Coen, Ethan Coen
Cast John Turturro, John Goodman, Judy Davis
Box Office $6,153,939
Why An essential entry — Barton Fink embodies exactly what this collection is about.
Adaptation.

Adaptation.

2002
5
Adaptation.
2002
5
Adaptation.
IMDb 7.7 / 10
Director Spike Jonze
Cast Nicolas Cage, Meryl Streep, Chris Cooper
Box Office $22,498,520
Why An essential entry — Adaptation embodies exactly what this collection is about.
Ed Wood

Ed Wood

1994
6
Ed Wood
1994
6
Ed Wood
IMDb 7.8 / 10
Director Tim Burton
Cast Johnny Depp, Martin Landau, Sarah Jessica Parker
Box Office $5,887,457
Why An essential entry — Ed Wood embodies exactly what this collection is about.
Get Shorty

Get Shorty

1995
7
Get Shorty
1995
7
Get Shorty
IMDb 6.9 / 10
Director Barry Sonnenfeld
Cast Gene Hackman, Rene Russo, Danny DeVito
Box Office $72,101,622
Why An essential entry — Get Shorty embodies exactly what this collection is about.
Living in Oblivion

Living in Oblivion

1995
8
Living in Oblivion
1995
8
Living in Oblivion
IMDb 7.5 / 10
Director Tom DiCillo
Cast Steve Buscemi, Catherine Keener, Dermot Mulroney
Box Office $1,111,790
Why An essential entry — Living in Oblivion embodies exactly what this collection is about.
Maps to the Stars

Maps to the Stars

2014
9
Maps to the Stars
2014
9
Maps to the Stars
IMDb 6.2 / 10
Director David Cronenberg
Cast Julianne Moore, Mia Wasikowska, Robert Pattinson
Box Office $350,741
Why An essential entry — Maps to the Stars embodies exactly what this collection is about.
La La Land

La La Land

2016
10
La La Land
2016
10
La La Land
IMDb 8.0 / 10
Director Damien Chazelle
Cast Ryan Gosling, Emma Stone, Rosemarie DeWitt
Box Office $151,101,803
Why An essential entry — La La Land embodies exactly what this collection is about.
Babylon

Babylon

2022
11
Babylon
2022
11
Babylon
IMDb 7.1 / 10
Director Damien Chazelle
Cast Brad Pitt, Margot Robbie, Jean Smart
Box Office $15,658,225
Why An essential entry — Babylon embodies exactly what this collection is about.
Once Upon a Time in Hollywood

Once Upon a Time in Hollywood

2019
12
Once Upon a Time in Hollywood
2019
12
Once Upon a Time in Hollywood
IMDb 7.6 / 10
Director N/A
Cast Leonardo DiCaprio, Jim Hemphill, Brad Pitt
Box Office $142,502,728
Why An essential entry — Once Upon a Time in Hollywood embodies exactly what this collection is about.

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