Perhaps 2% of the logos there could be taken at all seriously. The one which makes the A in GAP look like a pair of jeans is at least clever. But wow is there a lot of garbage there. Thanks for sharing the link!
I'd actually disagree. It's just a brand - your mind should associate the name and logo with connotations and feelings regarding their clothes and their shopping experience (and probably sex, it's a youthful clothing store). You shouldn't be thinking about what the word "gap" literally means - it's orthogonal to the meaning of the brand.
only moderately related, but the best thing Gap ever did was when they bought ads at a bunch of baseball stadiums on the outfield walls, so when ever someone hit a double to the gap thats what you'd see.
Being the person who ran the contest for 99designs. I have to agree there were a lot of average logos submitted, some very funny ones also. However there were also a hell of a lot of great logos and over 1000 designers participated in the contest. So all in all i think it succeeded in engaging with our community which was the idea behind it. To run a contest for the fun of it and let people work on something topical.