I don't know if it glitched on me, but I got this achievement a LOT earlier than I was meant to, and here's the process I used:
I played the game through until I had finished Case 3 and was wandering around North Peak picking up collectables, and went to the roof of the bar in the middle (I can't remember its name, but there is a power suit on the roof of it), collected the suit and dropped to the ground, entered the bar & used the video game as a power-up, then went to the 2nd video game and powered up again, and onto the third machine to power up... upon the 3rd video game machine I got the achievement!
As I said, I don't know if it glitched for me, but this might help someone else get the cheevie if they're having problems with it.