- Was the voice of both Hans and Fritz in "The Captain and the Kids" / "The Katzenjammer Kids" cartoon series for MGM.
- Rode in the Hollywood Christmas Parade with other child stars and Boris Karloff. When he accidentally kicked Karloff in the head, Karloff turned to Bobby and joked, "Not too many kids can kick Frankenstein and get away with it.".
- Sang at the Democratic Convention in Chicago for President Franklin D. Roosevelt.
- Got into show business using a letter of introduction from Charles Chaplin's wife, Mildred Harris.
- Attended Hollywood Professional School with other child stars at the time, including Donald O'Connor and Roddy McDowall.
- Was the newsboy signature voice on the "Big Town" radio show starring Edward G. Robinson for four years. Was also a radio series regular and close friends with Robinson.
- Was actually burned during the filming of the Republic serial Daredevils of the Red Circle (1939), and had to be rushed to a hospital.
- In the early '40s "Astrology Magazine" predicted two stars of tomorrow: Winkler and Ronald Reagan.
- Is featured in the movie comic book version of Gene Autry's western Blue Montana Skies (1939), in which he appeared.
- Father of William Winckler.
- As a child actor, he worked with most of the famous movie cowboys during Hollywood's Golden Age; Gene Autry, Roy Rogers, Wild Bill Elliott, Johnny Mack Brown, Tim McCoy, Bob Steele, Bob Livingston, Bob Baker, George Houston, George Montgomery, Wayne Morris, Dick Foran, Tom Tyler, Eddie Dean, Richard Dix, Dennis Morgan, Smiley Burnette, Raymond Hatton, Rufe Davis, Lou Fulton, Fuzzy Knight, Gabby Hayes, Dub Taylor, Andy Clyde, Ed Cobb, Tom London and Leo Carrillo.
- His career as a child star ended when he was about 20. He enlisted in the US military, and when he got out he became interested in law. He got his law degree and became a successful entertainment attorney, often representing the actors he worked with as a child.
- Played W.C. Fields' son on the "Your Hit Parade" radio show.
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