Lets start with the older movie

Basically this guy decides to set up a car rally/scavenger hunt

For some reason several stereo typical groups join in the race

They go to various locations all over town where he has hidden clues - while he keeps track of them via CB or telephone and spies all over town

It was really cheesy but great fun to watch - I wish I could remember the name


Newer title - movie very similar premise to the movie 100 girls

However in this movie he has an a-hole friend who when he finds out one of the girls the main character learned about in the apartment building has a vibrator hooked up to her pager - phones her when she is on air - they later hook up

The main character is looking for his unknown love - in one scene his unknown love supposedly leaves a butt print

Its set in an apartment building and I think he finds out about a pervert who had been spying on the girls in the building as well

The first movie you're talking about is Midnight Madness. I loved that movie when I was a kid. You're right, it was cheesy but still a fun movie! :)

Your second movie may be Girl Fever (http://www.imdb.com/title/tt0265010/) from 2000... written and directed by the same bloke what did 100 Girls. It features Jennifer Morrison, currently appearing on TV's House.