Hollywood

1950 · Billy Wilder · 110 min · Film Noir / Drama

Sunset Boulevard is one of those rare films that feels like it could have been made yesterday, even though it's over seventy years old. Billy Wilder crafted something vicious and beautiful here, a story about fame's wreckage that never flinches from its own darkness. Gloria Swanson's Norma Desmond is one of cinema's greatest creations, a character so vivid she's become shorthand for an entire kind of delusion. If you care about movies at all, this one demands your attention.

2012 · Ben Affleck · 120 min · Thriller / Drama

Argo turns one of the strangest true stories in espionage history, the CIA rescuing six Americans from revolutionary Tehran by disguising them as a fake sci-fi film crew, into a thriller of ruthless efficiency. Ben Affleck directs and stars with 1970s texture soaked into every frame, while Alan Arkin and John Goodman supply the Hollywood satire that makes the movie sing between clenched-teeth sequences. It won Best Picture, and it invented most of its climax, shrinking Canada's role and adding an airport chase history never provided. As drama, near-flawless. As history, printed legend, and it knows it.

2019 · Quentin Tarantino · 161 min · Comedy / Drama

Once Upon a Time in Hollywood is Tarantino's most relaxed and personal film, a sun-soaked love letter to 1969 Los Angeles that spends two and a half hours hanging out with its characters before unleashing a violent, cathartic finale that rewrites history. Leonardo DiCaprio and Brad Pitt have electric chemistry as a fading TV star and his stuntman, and the recreation of late-1960s Hollywood is meticulous to the point of obsession. The pacing is deliberately languid, with long stretches that prioritize atmosphere over plot, and viewers who need a story to drive forward will find the first two hours aimless. Margot Robbie's Sharon Tate deserved more to do. But as an exercise in mood, nostalgia, and the bittersweet feeling of watching an era end, it's one of Tarantino's richest achievements.

2017 · 3 Seasons · Epix · Comedy / Crime / Drama

Get Shorty is a sharp, darkly funny crime comedy about a Nevada hitman who moves to Hollywood to produce a movie and discovers that the entertainment industry operates by rules remarkably similar to organized crime. It's consistently entertaining across three seasons, with a standout lead performance and a satirical edge that keeps the Hollywood send-up from becoming toothless.

2020 · David Fincher · 131 min · Drama, Biography

Mank is a gorgeously crafted love letter to Old Hollywood that showcases Gary Oldman at his best, though its deep investment in industry politics and the Citizen Kane authorship debate may leave casual viewers on the outside looking in.

2024 · Amor Towles · 400 pages · Literary Fiction

A collection of six New York-set short stories and a novella set in 1930s Hollywood that showcases Amor Towles's trademark elegance and wit, though the shorter form reveals both his strengths and his limitations more starkly than his novels do.

2004 · 8 Seasons · HBO · Comedy / Drama

Entourage is a Hollywood fantasy machine powered by wish fulfillment, celebrity cameos, and Jeremy Piven's volcanic performance as super-agent Ari Gold. The first four seasons deliver a breezy, entertaining ride through a version of Los Angeles where everything works out for the main characters, and the fun is infectious when you stop resisting it. Later seasons run out of creative energy, and the show's treatment of women, always a weak point, hasn't aged well at all. It's a time capsule of mid-2000s bro culture that's simultaneously easy to binge and difficult to defend. If you can enjoy it for what it is without expecting it to be more, there's genuine entertainment here.