Here's the finds from the last couple months, I don't go out methodically to the thrift stores and pawn shops, but I try to stop at them while I'm in town for other things.
These are all of the controllers I've picked up, they are definitely my favorite thing to find.
2x Black Gamecube
1x Purple Gamecube
2x Blue Xbox S
1x Green Xbox S
2x Black Xbox S
1x Black Dualshock 2 (Have passed up like 20 of these in mint condition)
2x Smoke Black Dualshock 2
1x Platinum Dualshock 2
1x Blue Dualshock 1
2x Red Dualshock 1
1x Clear Dualshock 1
And a goofy agetec fishing reel controller
all either 4 or 5$ a piece
Here's the games I found.
Goodwill First
PS1
Ridge Racer Type 4
Need for Speed High Stakes
Wipeout
Jetmoto 2
Namco Museum 3 (not pictured)
Xbox
Call of Cthulhu
PS2
NFS: Most Wanted
WWE: Crush Hour
SnoCross 2
Freekstyle
Simpson's Road Rage (not pictured)
PS3
LittleBigPlanet GOTY Edition
all 3-5$ a piece.
Also got these 2 from a little tiny thrift store
Blitz the League 2 and Test Drive Unlimited 2
Marked 10$ a piece but they were buy one get one, not bad for 5$ each.