Surprised you didn't include this guy, yet I suppose he wasn't exactly good looking nor very well known.
https://en.m.wikipedia.org/wiki/Bugs_Moran
George Clarence "Bugs" Moran
George Clarence "Bugs" Moran (/məˈrɑːn/; Adelard Leo Cunin; August 21, 1893 – February 25, 1957) was an American Chicago Prohibition-era gangster. He was incarcerated three times before his 21st birthday. Seven members of his gang were gunned down and killed in a warehouse in the Saint Valentine's Day Massacre of February 14, 1929, supposedly on the orders of his rival Al Capone.
Moran was born Adelard Cunin to French immigrant Jules Adelard Cunin and Marie Diana Gobeil, Canadian descendent, in Saint Paul, Minnesota. He attended Cretin High School, a private Catholic school in Saint Paul, but he also joined a local juvenile gang and left school at age 18. He was later caught robbing a store and was sent to the state juvenile correctional facility, and was put in jail three times before he turned 21. He then fled to Chicago where he was caught trying to rob a warehouse, taking part in a horse-stealing ring, taking part in robbery involving the death of a police officer, and robbing a freight car, for which he received a variety of prison and jail sentences.