20. Entourage (2004)
Partly inspired by the life of Mark Wahlberg, one of the show’s executive producers, this series focuses on actors and agents as they navigate fame and wealth in Hollywood. Adrian Grenier stars as a talented movie star who is kept grounded in reality by his childhood friends. It hasn’t aged well, but as an insight into Hollywood in the early 2000s it is enjoyable.
Sky
19. Tropic Thunder (2008)
Ben Stiller’s rip-roaring Hollywood satire is a big-budget comedy stuffed with purposefully offensive material. The story is about a bunch of film stars who are dropped in a real-life jungle to shoot a Vietnam war movie. There’s Tom Cruise in a bald cap grooving to Flo Rida, and Robert Downey Jr playing a character who has a special dermatological operation to turn his skin black.
Amazon
18. 30 Rock (2006-13)
Based loosely on the backstage antics at the US comedy institution Saturday Night Live, this series stars Tina Fey as Liz Lemon, the head writer on a sketch show, opposite Alec Baldwin’s vice-president of the company. Fast-paced and chaotic, it was nominated for 22 Emmy awards in 2009, the most in a single year for a comedy series.
Amazon
17. BoJack Horseman (2014)
Who knew a cartoon about a talking horse actor could be so moving? Set in a parallel universe where humans coexist with talking animals, this story of Bojack the horse (voiced by Will Arnett), who has walked away from his showbiz career, is endearing. With pop star dolphins and jogging baboons, this show is one of the smartest animated shows on television.
Netflix
16. Episodes (2011-17)
How is it that the writer of warm-hearted Friends also penned this bitter comedy series? Starring Matt LeBlanc (Joey) as himself, the series explores the ghastliness of the TV industry in LA and the people who work in it. Stephen Mangan and Tamsin Greig play the husband-and-wife writing team transplanted to LA to work with LeBlanc. It’s not revolutionary, but it is certainly entertaining.
Amazon
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15. Mank (2020)
This remarkable tribute to the backstage lore of classic film follows the alcoholic screenwriter Herman J Mankiewicz (Gary Oldman), the co-writer of Orson Welles’s epic Citizen Kane. Led by Oldman’s excellent ruined performance, the film provides a fascinating insight into the life of the oft-sidelined writer, who didn’t get the credit he deserved. Tuppence Middleton gives a shrewd performance as his long-suffering wife, Sara. The film is a cinephile’s dream.
Netflix
14. Hail, Caesar! (2016)
This bonkers caper, written and directed by Joel and Ethan Coen, is set in 1951, at the height of studio power. A studio fixer (Josh Brolin) protects film stars from scandals, whether that’s out-of-wedlock pregnancies or being kidnapped by blacklisted communist screenwriters. It’s pure escapism, with strong performances from Scarlett Johansson, Ralph Fiennes and George Clooney.
Netflix
13. Lost in Translation (2003)
Two people form an unexpected bond in Sofia Coppola’s film. One is Bill Murray, who plays a Hollywood has-been, and the other is Charlotte (Scarlett Johansson), an anguished young wife.They strike up an oddball friendship in Tokyo. Wonderful comedy and tender romance combine to make something quite special.
Starzplay
12. The Player (1992)
A contender for the film with the most celebrity cameos — at 65, including Bruce Willis, Julia Roberts and John Cusack. It’s a thriller that mocks movie-making and stars Tim Robbins as a studio executive, troubled with death threats from a mysterious screenwriter.
Amazon
11. I Hate Suzie (2020)
From the Succession writer and playwright Lucy Prebble, this show-stopping series tells the story of a former child star, played by Billie Piper, who is offered the role of a lifetime, at which point her life falls apart — her phone is hacked and nude photographs are leaked online. A brilliant portrait of a modern celebrity, self-loathing and our soulless world. It’s back this winter.
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10. Curb Your Enthusiasm (2000-)
Still firing on all cylinders, Larry David’s offbeat sitcom has the Seinfeld creator playing himself, a semi-retired LA producer. It manages to get away with tackling everything from race to Covid. In April David confirmed the series will be back soon for a 12th season.
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9. A Star Is Born (1954)
Before Lady Gaga and Barbra Streisand, there was Judy Garland playing a young star on the way up. George Cukor’s heartbreaking tragedy pairs her with James Mason, who bounces brilliantly off her charged performance. Forget The Wizard of Oz, this is Garland’s finest outing.
Amazon
8. The Artist (2011)
This movie about the Hollywood silent era is itself almost entirely silent. Set in 1927, it follows Jean Dujardin’s dashing film star, who falls for a young actress. It was nominated for ten Oscars, winning best picture, best director and best actor for Dujardin.
Amazon
7. Birdman (2014)
In Alejandro González Iñárritu’s showbiz satire, Michael Keaton plays an actor once famed for his superhero roles. The film follows his attempt to claw back his pre-blockbuster heyday by staging a Broadway show. There are backstage punch-ups, emotional breakdowns and a supporting cast that includes Edward Norton and Emma Stone.
Disney+
6. Sunset Boulevard (1950)
Gloria Swanson is outstanding as Norma Desmond, a forgotten film queen who ensnares a struggling screenwriter (William Holden). Billy Wilder’s 1950 black comedy is a moving insight into Hollywood.
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5. Once Upon a Time in . . . Hollywood (2019)
Set in Los Angeles in 1969, Quentin Tarantino’s retro tour de force stars Brad Pitt as the stunt double of a fading actor played by Leonardo DiCaprio. It’s haunted by Charles Manson and his hippy followers, and Margot Robbie plays Sharon Tate, a Manson victim. An eclectic, sun-kissed triumph — although it is long, at more than two hours.
Amazon
4. Mulholland Drive (2001)
David Lynch’ s unsettling mystery catapulted Naomi Watts and Laura Harring to stardom. Watts plays a wannabe film star; Harring is Rita, a strange woman battling amnesia after a car crash. Together they attempt to find out Rita’s true identity. This gripping film looks beautiful and stays in your head long after the credits.
Amazon
3. Call My Agent! (2015-)
This French show became a word-of-mouth hit in the UK and charts the backstabbing and mishaps at a talent agency in Paris. With cameos from stars including Sigourney Weaver and Juliette Binoche, it is a charming insight into the world of showbiz.
Netflix
2. La La Land (2016)
Damien Chazelle’s love letter to the golden age of Hollywood stars Emma Stone and Ryan Gosling as Hollywood dreamers who fall in love while dancing their way across LA, and at one point among the stars of the Griffith Observatory.
Starzplay
1. Singin’ in the Rain (1952)
A glorious movie musical, full of charm and unforgettable numbers. Starring Gene Kelly, (who co-directed with Stanley Donen), Donald O’Connor and Debbie Reynolds, it is a sublime satire of Hollywood at the dawn of sound.
Amazon