'Undercover Brother' At 20: A Comedy Movie Rewind

“Can you play something funky for a brotha to drive to?”

Cue Kool & the Gang’s Jungle Boogie. B.R.O.T.H.E.R.H.O.O.D. agents Undercover Brother and Sistah Girl put the pedal to the metal as they try to outdrive The Man’s top agent: White She-Devil.

No. I’m not forcing you to listen to me talk about my dreams. I am simply recounting the 2001 film Undercover Brother. The soundtrack? Pure gold. The plot? Pure insanity! For the uninitiated, Undercover Brother is the tale of a group of Black spies who seemingly give up their real names for a cause greater than themselves.

Those spies are played by an all-star cast that includes Eddie Griffin as the Afro-ed Undercover Brother; Academy Award-nominee Aunjanue Ellis as Sistah Girl; Chi McBride as the Chief, Neil Patrick Harris as Lance the intern (affirmative action apparently benefits white people!), Billy Dee Williams as the General, and Dave Chappelle as Conspiracy Brother. A cast so good, I can’t even.

And that doesn’t even include the enemy of all Black people and culture: The (literal) “Man,” played by Robert Trumbull, who causes havoc with his other top agents, Mr. Feather, played to confusing perfection by Chris Kattan, and White She-Devil, played by Denise Richards.

On its 20-year anniversary, it’s time to ask: Has time been kind to Undercover Brother? Has it aged into an iconic comedy movie that pleases our palate (like a fine wine) -- or is it now a hot steaming mess of problematic jokes and premises (like cheese. Racist cheese).

Let’s take out our gold afro pics and comb through the good, the bad, and the problematic of this hair-raising film.

The Good

1. The movie universe.

The world of Undercover Brother is fascinating. In the UB universe, the idea of Black Power, the very concept of being Black and proud, all started in the 1970s. So to bring the Black man down, The Man devises evil plots like Steve Urkel, Dennis Rodman, and mayonnaise. The Man is more than a concept -- there really is a “Man!” And the film’s strong opening montage introducing all these elements does a great job not only of spilling all that exposition, but also letting you know that you are in for a silly good time.

2: The soundtrack.

That amazing collection of music features tracks from the aforementioned Kool & the Gang, the O’Jays, Mary J. Blige, James Brown (who has a BIZARRE cameo), and of course, Willa Ford, whose song “I Wanna Be Bad” serves as the perfect intro for White She-Devil (we’ll get to her soon, trust me).

3. Brisk plotting.

So smart on the writer's part. With everything moving at such a quick pace, we viewers can’t really stop and think about how crazy everything is. One minute Undercover Brother and Sistah Girl are falling down a secret passageway to the underground lair of the B.R.O.T.H.E.R.H.O.O.D;, and the next minute Undercover Brother is using his elongating platform shoes to grow really tall and hop an even taller fence. Keeping everything fast and loose makes every scene feel necessary. Undercover Brother also has a good action-to-comedy ratio, something like 40% action and 60% comedy. Which for this writer is the perfect proportion.

4. The cast.

The actors are out of this world! In 2001, most of these actors were not exactly in high demand. Neil Patrick Harris was in his post-Doogie Howser phase when he was just Neil Patrick Harris-ing all over the place. See the Harold and Kumar movies. But the actor who does a real star-making turn in this movie is Dave Chappelle. Chappelle is on fire in this movie! Watching Undercover Brother reminds us exactly how he was able to write, star, and produce his own sketch comedy show.

5. The presence of Denise Richards.

Casting Richards as White She-Devil is the right choice. She is totally believable as a white woman who would be unaware of her effect on Black men. And then you think: But does she? Richards strikes the right tone of innocent, but suspicious. Now, do I like the POV of a film that says when Black men date white women, they lose their street cred and have now “sold out?” No sir, I do not. That’s why we need to turn up Willa Ford’s “I Wanna Be Bad,” and check out what’s bad about Undercover Brother.

The Bad

1. Seventies slang.

There. Is. So. Much. BAD! Because Undercover Brother harkens back to 1970’s blaxploitation films, there’s a lot of throwback lingo that does not work. “Dissed.” “Soul.” “Right on.” It’s dated to the point of being confusing at times. To be cool you have to use slang from the seventies? Since when?

2. Billy Dee Williams.

I know. Destroy me, drag me, whatever. I have YET to be impressed by a Billy Dee Williams performance and Undercover Brother hasn’t changed my mind. Maybe a lot of his good stuff ends up on the cutting room floor, but damn y’all, Mr. Dee Williams is sleepwalking through this whole movie. Essentially, BDW plays a Black general who The Man kidnaps and brainwashes, and it’s up to the B.R.O.T.H.E.R.H.O.O.D. to save him. Or to get him some coffee so Billy Dee can wake up and make a choice as an actor. Any choice at all. God, watching BDW in Undercover Brother is eerily similar to watching him in Tim Burton’s Batman. He’s the same in everything. He exists to remind us of The Empire Strikes Back. That’s it.

3. The forehead-slapping MacGuffin.

And speaking of Billy Dee… I think it’s time we talk about the MacGuffin of Undercover Brother. Apparently, the way to keep the Black man down is best done by having Black celebrities eat mind-controlling fried chicken. And once the hypno-chicken is consumed, the Black celebs start making more pro-white content. Like Terry McMillan’s sequel: How Stella Got her White Man Back.

Ah, where to begin? The idea that Black people would be controlled by fried chicken is obviously offensive. But this was back in the day when “offensive” was considered good. To be “offensive” meant you were pushing the boundaries of what comedy could be. From the vantage point of 2022, I hope we know now that upholding a stereotype will only be seen as satire to those that don’t need to be told it’s satire in the first place. For the rest of the world, it really reinforces the idea that to be Black is to be a part of a monolith. That we move as one unit. Hence the B.R.O.T.H.E.R.H.O.O.D. Not great. And Undercover Brother does a lot of racial monolith-ing all over the place. All Black people like fried chicken, all Black people like rap, all Black people like hot sauce, and all Black people hate mayo and Michael Bolton.

Not only do these stereotypes separate white and Black people, they also confuse young Black people watching. Like me! I don’t mind Michael Bolton. Do I have to give up my skin color? And I’ll eat mayo in a pinch. (Although if I’m being honest, it is the nastiest thing I’ve ever tasted and I’d rather eat literally anything else! So maybe UB got that part right.)

4. The white people.

We gotta talk about the white people in this movie. It’s wild to me how racist everyone was. I mean, I get it. Most of the white people in this movie worked for The Man and wanted the downfall of all Black things and people. But not everyone worked for The Man! There are so many scenes with white people being casually racist with no repercussions. Like the bizarre scene at a clothing store when Undercover Brother shouts at Sistah Girl, then an intercom alerts everyone to an angry Black man in the store. Funny, but also tragic because the white people never get their comeuppance. We never see the white people come to terms with their ignorance so the message is “white people are hopeless and will always be racist and will never see Black people fully.” This is a grim view, one that feels very 2001. I think we should show that white audiences must learn and grow, and not in the way NPH’s character Lance grew -- by watching one viewing of Roots, apropos of nothing, and suddenly “getting” racism. It’s wild in these streets, folks.

Even wilder? The problematic and unforgivable parts of Undercover Brother.

THE PROBLEMATIC:

Oh boy. This movie is a woke snowflake's nightmare! The difference between bad and problematic is that bad means something just doesn’t work at all. And problematic refers to things that were once considered good but are now so dated they’re almost offensive. And I think we gotta start with that number 1 sucker: Chris Kattan.

1.Chris Kattan.

Chris Kattan’s performance as Mr. Feather is the most confusing performance the world has ever seen. Even more confusing than Keanu Reeves’ performance in Something’s Gotta Give. (Keanu as a doctor? Dream on, Hollywood, I ain’t buying it). In Undercover Brother, Kattan plays a foot soldier of The Man who outwardly HATES Black culture and diversity … but he secretly wants to be a part of it. And Mr. Feather hates himself for loving Black culture. It’s internal agony for him. On paper, I actually think it’s a great character description. The execution, however, is confounding. In portraying a white man who loves Black popular culture, Kattan reads as gay to me. (Which is fine, because I am gay.) But Kattan is not. No matter how many times I’ve checked, he’s not. So we are left to watch him fail to resist the old school bounce of Mary J. Blige's Family Affair. Let’s get it bumping indeed, Kattan! I don’t quite know how to feel about Kattan keeping his appropriation of Black culture a secret. Kattan’s journey as Mr. Feather is fascinating because I have no idea how to do it the right way.

2. Neil Patrick Harris.

We get more odd character choices from NPH. To show that his character Lance isn’t down for the cause, he scream-sings Christina Aguilera’s What a Girl Wants. Again … that’s a gay thing. Undercover Brother conflates white culture and gay culture too much for this gay writer’s liking. The two are not synonymous. If it involves pop singers, dancing, or crisp lines in your pants, that’s gay. If we’re talking about Wayne’s World, trips to Wisconsin, or Ray Romano -- that’s white culture.

3. Cartoony racial tone.

The racial tone is so comedic that it diminishes the truth of the matter. The FBI did spy on Martin Luther King, as well as orchestrated the death of Black Panther leader Fred Hampton. Highways were built in Santa Monica, California, in an effort to force Black residents to move. And of course #OscarsSoWhite. To put these real-life examples in the mouth of Dave Chappelle’s “Conspiracy Brother” diminishes the real harms of racism in America and makes it all seem like a joke. I mean, do I need to go any further than THE MIND-CONTROLLING FRIED CHICKEN?!

I know it’s a comedy. But living in the 2020s, I believe too much comedy can create complacency in society.

The Verdict

After all is said and done? This movie slaps. Let’s keep it. While there is a ton of dated humor and ideas, Undercover Brother still delivers on its universal and timeless message of equality, inclusion, and staying true to your funky self. And we will just find a way to overlook the cringey moments.