Nobody's Perfect (1990)

Chad Lowe has always been a pretty boy, but he was never prettier than he was in Nobody’s Perfect (1989). If you know the famous last line in Some Like it Hot (1959) you should be able to guess that this one's a crossdressing comedy. Yes, Rob Lowe's brother Chad plays Stephen, a college tennis star who is obsessed with female player Shelly (Gail O'Grady). The problem is, Shelly doesn’t even know Stephen is alive. After his grades drop and his tennis game suffers, Steve is kicked off the team. But as luck would have it, his goofball friends hatch a plan that has cutie Chad cross dressing in hilarious Shakespearean fashion in order to get closer to his ladylove. Suddenly, Stephen has become Stephanie: a dominant female player who ends up rooming with Shelly. Classic crossdressing hijinks ensue, including a gambling scandal, trouble with some horny dudes, and even a bunch of peeing while standing up jokes that were so similar they just might have been ripped off by Mrs. Doubtfire (1993) four years later. What a racket! But none of that's as good as the laugh-out-loud funny bubble bath scene. Chad, looking far more like Ozzy Osbourne than an actual woman, Gail walks in and starts splashing some water right where his cock is, although he's covering it up with a rubber duck. Quack, quack, if only we got to see his sack! Later we'll get some upskirt action when Chad falls over trying to put on some pantyhose. His ass looks great, even if he does a great job covering up his manhood! He's not on the tennis court, but he's still serving! Nobody's Perfect, but those skin scenes are perfectly adequate to add to your spank bank!