Less Than Zero
This was the second of three films featuring James Spader and Robert Downey Jr. The first was 1985's Tuff Turf and the third is 2015's The Avengers: Age of Ultron. It was also the third of three films featuring James Spader and Andrew McCarthy. The first movie was Pretty in Pink and the second picture was Mannequin. All three titles were first released during 1986-1987.
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