Top 10 Hollywood Movies About Hollywood

Hollywood is Hollywood’s biggest fan. There are dozens of films about films and the film industry, as most recently showcased by Once Upon a Time in Hollywood. While not all of these films are huge successes and are largely self-serving, many of them are quite good. Let’s take a look at the top ten Hollywood movies about Hollywood:

Honorable Mentions

Argo

Shrek 2

Barton Fink

Who Framed Roger Rabbit

Teen Titans Go! to the Movies

The Disaster Artist 

#10: Tropic Thunder (2008)

Image via Entertainment Weekly

2008 was a phenomenal year for Robert Downey Jr. Not only did the actor rebound with his (now) most iconic role in Iron Man, but he also played a man playing a black man in Tropic Thunder. Downey isn’t the only A-lister here though. Downey is also joined by Ben Stiller and Jack Black in this satire of both the Vietnam War and the Hollywood actor’s life. This film is hilarious and bizarre from the get-go, never letting up on its absurdity. Though not a massive success compared to its budget, this is one of the most well-regarded and iconic roles of each of its leads’ careers. It’s so iconic in fact, that it’s probably the most quotable movie on this list.

#9: Who Framed Roger Rabbit? (1988)

Image via Film

Speaking of absurd movies…

The Disney/Warner collaboration that finally put Mickey Mouse and Bugs Bunny together on screen is about as absurd as it gets. While noted primarily for its actors and over-sexualization of Jessica Rabbit, this movie has so much more going for it. For example, Who Framed Roger Rabbit? uses its Toontown lens to lampoon Hollywood itself. We get to see some of our favorite cartoon characters “behind the scenes” and living their normal lives. Roger Rabbit’s faux Hollywood is looney, wacky, and too much fun to not land it on this list about Hollywood’s greatest attempts at self-examination.

#8: Sunset Boulevard (1950)

Image via Taste of Cinema

Sunset Boulevard is definitely dated, but it still hasn’t become irrelevant. This harrowing tale of a down on his luck writer and an actress of a bygone era is still chilling to this day. While the Hollywood that Norma Desmond misremembers is long gone today, Sunset Boulevard makes it feel startlingly familiar. This movie is filled with suspense and touching goodbyes to a very unique and oft-overlooked era in Hollywood. The day of the “talkies” may be dominant, but it’d be nothing without the silent era that started it all.

#7: Boogie Nights (1997)

Image via Mental Floss

You might be thinking, “Hey, Boogie Nights is about porn, not Hollywood”. You’d be correct, but it’s a movie about porn that is centered in and around Hollywood. Paul Thomas Anderson’s breakthrough hit doesn’t get as much love as it should in the twenty-two years since its release. Not only does it boast an incredible cast of then up and comers, but it’s entertaining as hell. Boogie Nights dissects the nitty-gritty, grim reality of the lives of not only porn stars, but stars in general. It’s an off-putting look at what the industry does to those who choose to be a part of it.

#6: Hail, Caesar! (2015)

Image via Time Magazine

Hail, Caesar! isn’t one of the Coen Brothers’ most beloved films, but it should be. George Clooney, Channing Tatum, Ralph Fiennes, and half a dozen others star in this tribute to the silver age of cinema. It’s a love-letter to an era where epics such as Ben-Hur and The Ten Commandments ruled the day. The Hollywood of Charlton Heston, Dean Martin, and Marilyn Monroe is on display here, and it is hilarious. The film has some great musical numbers, as well as some interesting takes on what it meant to be a studio star back in the day.

#5: Once Upon a Time in Hollywood (2019)

Image via CNN.com

Once Upon a Time in Hollywood might just be Tarantino’s best. It’s a deep look into the life of a Hollywood star and the pains of how short a Hollywood career often is. It’s a hilarious comedy that breaks down the goofiness of classic TV, the silver age, and the legends who acted through it all. Tarantino’s world of the bygone L.A. is explored greatly but leaves enough unexplored that you just wish you could have stayed in it a little longer.

#4: La La Land (2016)

Image via Jezebel

Hollywood isn’t an easy industry to break into. Most who try to break into the world of cinema end up getting broken by it instead. Damien Chazelle’s La La Land is not just a phenomenal musical, but it’s a terrific look into the breaking of a person before their big break. It’s got heart and oh-boy does it hurt watching Mia and Seb choose success instead of each other.

#3: The Muppet Movie (1979)

Image via IGN Entertainment

Who would have thought that Muppets could disassemble Hollywood so well? Kermit’s journey to stardom takes him through a rather fairytale version of Hollywood, but it takes him through Hollywood none the less. Wouldn’t it be nice if the studios really gave out the standard rich and famous contract like candy?

Anyways, its time to get movin’ right along to the next on this list of Hollywood movies about Hollywood.

#2: Singin’ in the Rain (1952)

Image via Hollywood Reporter

Another classic on the list, Singin’ in the Rain pays homage to the same Hollywood era that Sunset Boulevard does. The Gene Kelly classic pays homage to itself as it walks its characters through the silent era and into the loud and whimsical era of the Silver age. With charming performances from Kelly and Debbie Reynolds, this film takes a fun romp through the trials and pitfalls of stardom and how movies get made. There aren’t many more Hollywood movies about Hollywood that are as obsessed with the process as Singin’ in the Rain.

#1: The Nice Guys (2016)

Image via Roger Ebert

The Nice Guys both is and isn’t about Hollywood. In the vein of Boogie Nights, it focuses primarily on the porn industry based around L.A. in the sixties and seventies. It’s an underrated buddy movie between Ryan Gosling and Russel Crowe as they try to unravel the mystery behind the death of Misty Mountains, an illustrious porn-star. It’s a hilarious movie that tries to highlight the artistic sense of porn, if there even is one, while lampooning Hollywood and the porn industry in the process. The Nice Guys also takes the cake for Robert Downey Jr.’s best cameo, if you can spot it.

Coincidentally, this is the second time both Ryan Gosling and RDJ appear on this list, it’s almost as if they have a knack for this whole Hollywood thing.

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