Pitch (1997)

A Canadian documentary featuring two young filmmakers attending the Toronto Film Festival to pitch a film concept to various celebrities. Their film idea, titled "The Don", concerns a Mafia don who goes for a hernia operation but gets a sex change instead. During the 1996 Toronto Fest, they approach Roger Ebert, Norman Jewison (at a packed press conference), Eric Stoltz (leaving a limo), Al Pacino, and others without much success. On a roll, they leave Toronto for Hollywood, getting advice from Arthur Hiller and Neil Simon and finding an agent who expresses interest in their pitch.

Unfortunately the movie Pitch is not yet available on HBO Max.