Its bit of a long shot but I am wondering if anyone can help me identify a game I played in 1999. The game may have been older than that date. I think it was one of the first games I ever downloaded from downloads.com now download.cnet.com. It may have been free or a demo.

Basically you play as a mob boss/gangster and I remember there were lots of mini games in it where you do robberies and avoid the cops. I remember you could hire henchmen and "work" regular jobs to earn money which would fast forward time.

The graphics were really bad, 2D pixel art. It looked and played a lot like the 2013 released "Organ Trail" https://en.wikipedia.org/wiki/Organ_Trail (not to be mistaken with the classic Oregon Trail).

Hm,...if it literally (!) looks like "Organ Trail", it might rather be an 80s game..?

However...maybe: "The Godfather" (1991)? https://www.youtube.com/watch?v=iyM7NG2xZ0c
(though I personally wouldn't call those graphics "bad",...but hey: that may just be me) :)

King of Chicago?

You mean Abe Froman?

Could it possibly be the paradoxically named "Crime Fighter"?

https://dosgames.com/game/crime-fighter/

https://www.pssoft.de/english/index.html

https://www.youtube.com/watch?v=hX333N4czvo

Gangsters: Organized Crime ?.

Legal Crime ?

https://www.mobygames.com/game/21021/legal-crime/

https://www.youtube.com/watch?v=nVTh-ClRKdY

Wow, that's it! Thanks for that. I've been trying to identify Crime Fighter for years lol. Looks like it was released in 1993.

Thanks to the other people who made guesses. Those are other cool games to check out.