Judgment

To get this achievement you will have to play all arcade games (difficulty doesn’t matter) at both Club Sega’s and at your Detective Agency. Here’s a list of all games that are exclusive to those places
Club Sega on Nakamichi Street:
Fighting Vipers
Fantasy Zone
Virtua Fighter 2
Virtua Fighter 5

Club Sega Theater Square:
Kamuro of the Dead - Downstairs
UFO Catcher - Downstairs
Motor Raid - Upstairs
Darts - Upstairs
Space Harrier - Upstairs

Yagami Detective Agency: (Most likely not needed but keeping it here just in case the achievement doesn't pop for whatever reason. According to TA user: Sir Spink they unlocked the achievement without doing this minigame.)
Outrun

Note: Exiting the game and finishing your playing of it will count it as 'played'/'completed. So your last game will require you to finish it/back out of it to pop this achievement.