Hugo Pool (1997)

Hugo Pool (1997) isn't a designer swimming hole, but rather the moniker of hot minx Alyssa Milano, who stars in this quirky day-in-the-life of a virginal pool cleaner. Yes, Alyssa is that never-been-touched cherry, but she loses it to crippled Patrick Dempsey in a tantalizing sex scene where her assets are briefly uncovered. They make an appearance earlier in the film, when Alyssa is showering behind the opening credits, but her nipples are always just out of sight. While Hugo Pool is filled with major stars, including Sean Penn playing a leprechaun, it's Alyssa who delivers the gold at the end of this randy rainbow.