Once Upon a Time in Hollywood (2019)
The boys are back for part two of the Born to Watch fourth birthday celebration, and this week’s feature is Quentin Tarantino’s love letter to a vanished era, Once Upon a Time in Hollywood Review. Set against the backdrop of 1969 Los Angeles, this is Tarantino at his most nostalgic, most personal, and possibly most indulgent, but when it looks this good and feels this immersive, who cares?
Whitey, Damo and G-Man dive deep into the neon-soaked streets of old Hollywood, where television cowboys still mattered, stuntmen drank beer on rooftops, and everyone smoked enough cigarettes to shorten their lifespan by 20 years. From Rick Dalton's crumbling confidence to Cliff Booth's effortless cool, the crew break down why this film becomes richer with every rewatch.
The boys discuss how the movie completely subverts expectations, especially if you walk in expecting a full Charles Manson story. Instead, Tarantino delivers something far more emotional and reflective, a fairy tale about fading relevance, friendship, loneliness and the death of an era. Whitey explains how his first viewing left him confused, but his second cinema trip completely changed the way he saw the film, shifting focus away from the Manson backdrop and onto Rick Dalton's fear that Hollywood has passed him by.
There's plenty of love for Leonardo DiCaprio's performance as Rick Dalton, with Damo calling it one of the actor's best ever performances. The boys unpack how brilliantly DiCaprio balances insecurity, desperation, and ego, especially in scenes where Rick spirals after forgetting his lines or fearing he's become yesterday's news. Brad Pitt's Oscar-winning turn as Cliff Booth also gets the praise it deserves, with the crew debating whether Cliff might actually be one of Tarantino's coolest characters ever.
Naturally, the conversation turns toward the ridiculous depth of the cast. From Margot Robbie as Sharon Tate to Al Pacino, Timothy Olyphant, Dakota Fanning, Austin Butler, Luke Perry, Damian Lewis, Bruce Dern and Australian actor Damon Herriman as Charles Manson, this movie is stacked from top to bottom. The boys even debate whether this is Tarantino's deepest cast ever assembled.
And because this is Born to Watch, things quickly descend into absolute chaos.
There are discussions about Playboy Mansion parties, giant murals of yourself in your garage, Strangles learning what a queef is, and whether anyone alive could realistically resist picking up Margaret Qualley and Sydney Sweeney hitchhiking on the side of the road in 1969 Hollywood.
The episode also covers:
- Tarantino's recreation of 1969 Los Angeles
- The unbelievable soundtrack and radio advertisements
- Why the movie feels like it was made in the late '60s
- The brilliance of the Spahn Ranch sequence
- The film's Oscar success and controversial losses
- Why the ending works so perfectly
- Brad Pitt's effortless charisma
- Margot Robbie is somehow becoming even more beautiful in every scene
- The insane amount of smoking throughout the film
- Why Tarantino's "fantasy history" trilogy keeps working
There's also another loaded Snorbs Report Special, some underrated 2019 movie recommendations, and more random nonsense than should legally fit into one podcast episode.
Whether you're a lifelong Tarantino obsessive or someone who only recently discovered Once Upon a Time in Hollywood, this episode celebrates everything that makes the film unforgettable: the atmosphere, the performances, the music, the humour, and the strange, bittersweet feeling that Hollywood itself was changing forever.
So if you love movie deep dives, behind-the-scenes trivia, outrageous tangents, and three Aussie blokes talking absolute rubbish while somehow stumbling into genuine film analysis, this is the episode for you.
JOIN THE CONVERSATION
- 💬 Is Once Upon a Time in Hollywood Tarantino's best-looking film?
- 💬 Was Brad Pitt or Leonardo DiCaprio better?
- 💬 Did the ending completely catch you off guard the first time?
- 💬 Is Cliff Booth secretly Tarantino's coolest character ever?
- 💬 And how many cigarettes were actually smoked during this movie?
- 🎧 Listen now on Spotify, Apple Podcasts, and everywhere good podcasts live.
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