Director Peter Billingsley started off his film career by playing the young memorable character Ralphie in A Christmas Story (1983). He has had random cameos and producer credits in such films like Iron Man (2008), The Break-Up (2006), and his directorial debut, Couples Retreat (2009), which starred Vince Vaughn, who he has known since childhood.
Life insurance does not payout if the policyholder dies as a result of criminal activity as would be the case in the film. Further life insurance generally takes effect immediately upon completing the underwriting and paying the first premium.
Goof, not a point of trivia. The Honda Cate Barrow (Hailee Steinfeld) drives when Nick Barrow (Vince Vaughn) is being arrested by Braydon (Terrance Howard) has rims, no hubcaps. When there is twenty-one minutes left of the movie, you will see that the car has hubcaps on it after the gunfight.