I thought I'd add a little research to what's been mentioned above. Unlike Happy Stomach, I didn't visit all the places on the same day. But I did make careful mental notes. I'm partial to cheese fries made with Merkt/Merkt-style cheddar cheese. So Herm's, Susie's, other places that use nacho cheese (blech!) are out in my book. I had family in Highland Park growing up so I ate at Michael's (formerly Nathan's) quite a bit and I held them as cheese fry model in my mind. So, I was surprised to find they didn't hold up in the tasting. I still need to make repeat visits to Poochie's and Stash's (places I've had good cheddar fries in the past).
Here are my recent notes:
Little Island: Appear to be fresh cut fries but a little soft and limp when coated with the cheese. Cheese not as sharp as I like.
Grade: solid 'B'

Michael's: Like I said, these were my nostalgic ideal but the fries just didn't hold up. Not sure if these are fresh cut, but they didn't taste like it. The fries were really limp. Nice sharpness to the cheese and I do like the way they smush the cheese onto the fries to saturate them. Maybe because I had such high expectations, these really didn't do it for me. Note that I did get these to-go but I immediately tried them/photographed them after receiving them, so it wasn't a travel issue.
Grade: B-

Weiner and Still Champion: Really perfect slightly thinner-cut fries. Perfect crispness. Nice sharp cheese. I'm a cheese-glutton and I would have liked a little more cheese to saturate these fries. I must say though, the combination of cheese and garlic-aioli was quite nice (and I'm a cheddar fry purest). These were excellent.
Grade: A

The Weiner Circle: Thicker fresh-cut fries absolutely smothered in sharp Merkt cheese. These fries attracted attention from other customers. The cheese here was absolutely perfect (though I preferred WASC fries themselves by a slight margin). I'm ashamed to admit, I couldn't finish these

.
Grade: A

A+ would be WASC fries with the Weiner Circle cheese application.