This week, Phillips held its “GAME CHANGERS” watch auction in New York, where $20 million worth of vintage and specialty pre-owned watches were sold. Some timepieces were especially notable for the individuals who once owned them, including Marlon Brando, legendary golfer Jack Nicklaus, and Avengers' own Tony Stark.

According to GQ, Marlon Brando's rare Rolex GMT-Master, which the actor wore in Apocalypse Now, had long been thought lost by collectors. Thought of as "one of the most famous watches in the whole world," especially after Hodinkee included it in its list of 12 of the Greatest Missing Watches, the legendary timepiece finally surfaced this year after Brando's daughter found it and gave it up for auction. True to its legend, the watch fetched an astounding $1.9 million.

The same night another incredible piece sold. A gold Rolex Day-Date owned and worn for the 50-some years by the Golden Bear himself, golfer Jack Nicklaus eventually sold for $1.2 million. The piece that Robert Downey Jr. wore as Tony Stark in Avengers: Endgame, made by the Swiss techno-freaks at Urwerk reached a final selling price $250,000. Fitting for a piece from the year’s biggest movie.

You can check out our roundup of the rarest timepieces to hit Phillips' 2019 auction block here.

On this episode of The Dropcast, we are joined by Luke Fracher, who makes up a third of Round Two, a men’s boutique that aims to offer the best deals on clothing.

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