Hollywood Shuffle was the first film written, directed, produced by and starring Robert Townsend.  The autobiographical tale is simple enough; a young black actor finally gets his break in the Business, winning the part of the lead pimp in a ‘black’ mashup of West Side Story.  The role is so brutally stereotypical though, he wonders if he’s selling out his race just to get ahead.  Before anyone sends me a note in all caps asking ‘HOW IN THE BLUE HELL IS HOLLYWOOD SHUFFLE SO LOW ON YOUR LIST?!?”, I ask you to read the tale of the tape…

Relevance:  My counter argument begins here.  According to my ranking system, there are only 2 films in my ’25 Best’ breakdown that are either equal to or ranked higher than Hollywood Shuffle in this category.  The plot alone would rank it high in this category; the cast (which included besides Townsend a young Keenen Ivory Wayans and a younger John Witherspoon) adds to the relevance category; and the actual devices used in the movie (more on that later) make Hollywood Shuffle one of the most relevant black films ever made.

Legacy: For the sheer number of talents who appeared in this film, I would argue Townsend and Wayans are the only two who truly ‘jumped off’ to the next stage based on Hollywood Shuffle.  The story of ‘how’ this film was made (Townsend putting the half the $100,000 budget on personal credit cards, getting the crew to wear UCLA shirts since the cops rarely harass ‘students’) is as much part of Hollywood Shuffle’s legacy as anything else.

Craft: OK friends, let’s be honest with each other.  How many of you really remember this movie because of the plot?  How many of you even remembered the plot before I spelled it out in the first paragraph?  How many scenes can you quote from that revolved around the ‘plot’?  Even those of you (like me) who love this movie know good and well the ‘story’ is not why you love this film.  It’s “Winky Dinky Dog,”, it’s the black “Siskel and Ebert,” “Black Acting School,” “Jheri Curl,”…man I could go on, but the point is the skits that make up the film are what Hollywood Shuffle stand out.  And there’s nothing wrong with that, but it means compared to other ‘films’, Hollywood Shuffle has trouble keeping up.

Crossover: Whew, another rough category in my opinion.  Even with the number of classic skits in this movie, I can’t recall one white (or Hispanic or Asian) friend of mine ever talking about this film.  If you look back at the course of Robert Townsend’s career, I don’t know if he ever had the goal of crossing over to the mainstream, so you can’t fault somebody if they’re not really trying. But this is the crossover category…

Apollo: Some of the skits are naturally funnier than others, but the ‘interrogation of Jheri Curl’ still gets me to laugh out loud every time.  For those of you haven’t seen the movie, Jheri Curl (played by Keenen Ivory Wayans) turns out to be the killer of this young cat, but he won’t confess until he gets his curl activator taken away and his hair starts drying up…oh, just YouTube it (or better yet, watch the whole movie on Hulu (and no I didn’t get paid for that plug.))

So the hits keep coming.  Come back in a few weeks for my next pick, which might also be seen as ‘controversial’ in a different light…