Tootsie (1982)

Our 400th consecutive episode... who'd have ever believed it! And to celebrate, we're turning to movies that continue a tradition that dates back to Shakespearean times - Men dressing as women! First up, directed by Sydney Pollack (who also plays a role in the film... more on that in the episode) comes the story of Michael Dorsey (Dustin Hoffman), an actor who's just a little too opinionated about his craft, to the point where no one will hire him. To prove a point, he makes himself up as a woman who calls herself Dorothy Michaels, and auditions for a daytime soap opera. To his surprise, he lands a recurring role and becomes one of the most popular characters on the program! Along the way, however, he has to deal with gorgeous female co-stars and a tongue-kissing legacy leading man (played by George Gaynes). The biggest surprise, however, is Michael falling in love with his co-star Julie Nichols (Jessica Lange), while her father Les (Charles Durning) is falling for "her!" It's a comedy that also has some wonderful dramatic moments as well, and is the perfect combination of talent, writing, and directing to serve as our 400th episode! Also starring Dabney Coleman, Teri Garr, and Bill Murray!