Of course I would have to begin with the squint. Gould wields his squint as expressively as Del Toro in this performance. Sometimes it's incedulous, others it cynical, with a hint of bemused mirth.
Much like Elliot Gould himself once represented, Benecio Del Toro represents a sort of mainstream/counter culture hero (risking oxymoronic tightrope balancing here). Basically, the kind of guy who doesn't blindly accept the status quo, but punches holes in it in subtle and self amusing ways. A similar moment for Gould would be the moment he brings out the olives for the very un-military Martinis in "MASH."
Other aspects of the performance might be a product of Gould playing Marlowe and not necessarily aspects of Gould himself (although there are other filmic references to these aspects over Gould's career). Such as the coolness of the rumpled man, a guy who, on the surface might not look as unflappable as he actually is, thereby allowing his protagonists to underestimate him. Also that a cool guy might actually be sensitve. Benecio Del Toro is the only modern actor that I could picture getting up at two in the morning to get wet cat food at Ralphs (much as Gould did in the "Long Goodbye").
Hope this helps. Not really to be taken seriously, but just something to think about.
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