Rounders - https://www.imdb.com/title/tt0128442/ While the film is centered around poker and not trading it has elements/characters that deal with being conservative and also increasing your stake when the odds shift even further in your favor from your basic edge.
What does that comment mean in English? Although not a Hollywood movie, I thought the youtube documentary Floored was done pretty good and enjoyed watching it.
"The secret of a great fortune made without apparent cause is soon forgotten, if the crime is committed in a proper way."
While a documentary, I found Betting on Zero amusing: https://www.imdb.com/title/tt3762912/?ref_=nv_sr_1 Bill Ackman getting personally invested with bringing down Herbalife, the lesson for traders being, don't mix emotions with trades. Herbalife is a POS company but the stock market isn't the place to fight that battle.
Thinking, that there's still someone here, who haven't seen it yet, has no edge, but, lets try : I like this one as well :