Last Updated on October 10, 2025 by Matt Staff
The Roaring Twenties moved fast, with jazz in the air, secrets behind heavy doors, and nights that felt bigger than the rules. These mugshots pause that rush for a second and let the room go quiet.
Each face carries its own mood: a grin, a glare, a “don’t ask” shrug. Put together, these mugshots feel like the city catching its breath between the party and the headline.
1. Mr. Skukerman had an intense look
2. The scar on Mr. Jones’s face gave him away
3. This man was charged with bank robbery
4. This man was arrested in Australia for having two wives
5. Apparently, Mr. Riley is happy to be in jail
6. The murderer Eugenia Falleni, also known as Harry Crawford
7. This little guy is too young to be in prison
8. Crime boss, Tilly Devine
9. Mr. Cahill had a peaceful way of facing detention
10. Richard Loeb and Nathan Leopold, after murdering 14 14-year-old Bobby Franks
11. Don’t you dare to mess with Mrs. Smith
12. George Remus, the successful lawyer who became “the King of the Bootleggers”
13. That’s a lot of style for a photo, given the circumstances
14. Mrs. Dorothy Mort murdered her lover
15. Nice hair, Mr. Murray
16. Frankie Yale, American gangster and second employer of Al Capone
17. That’s what you call going down with glam
18. Mr. Evans is 1920s Steve Carell
19. Mugshot or fashion shoot?
20. Mrs. Osbourne is wondering when this would be over
Explore more historical content:
Loved this dip into photo-archive grit? Keep the nostalgia going with these 20 Photos Of Depression-Era Gangsters, or these 20 Lesser-Known Tales About Criminals from the 1990s. You can also check these 15 Stories About Members of the 27 Club.
