When Romance Met ComedyWith When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.  

Eddie Murphy is kind of a dreamboat. That can be hard to remember after the decades in which he settled into (or perhaps settled for) a career in broad comedic roles in lackluster family films. Indeed, it can be especially hard to remember if, like me, you were part of the generation that knew Murphy as the Nutty Professor and Donkey from Shrek long before you ever saw his red leather jumpsuit-clad standup act. Yet in between his explosive comedic debut and middle-aged comedic acquiescence, Murphy released a film that displayed the full potential of his romantic leading man charisma. And the way it was received just might be the key to understanding the subsequent arc of his career.

Give or take how you classify Coming To America (it’s structured around romance, but I’d call it more of a straight comedy), Boomerang is Eddie Murphy’s only foray into the true romantic comedy genre. It’s also one of his few films in which he just plays a normal guy. Successful advertisement executive Marcus Graham may be a womanizer, but Murphy channels Cary Grant more than the Roxbury Guys. When Marcus delivers a lie about catching his fiancée with the best man and the priest on his wedding day, it’s with the grounded demeanor of a guy trying to sell himself as heartbroken, not a comedian trying to sell the ridiculousness of a joke. Murphy’s still hilarious in the film; it’s just in a much more low-key, naturalistic way. Marcus soon gets a taste of his own medicine from his new man-eating boss, Jacqueline Broyer (Robin Givens), all while becoming best friends with artsy, empathic Angela Lewis (Halle Berry, still a relative unknown). As those experiences change Marcus for the better, Murphy gets a chance to stretch his dramatic wings, too.

Boomerang was specifically designed to give Murphy a different, more three-dimensional role than the explosive performances that had made him a blockbuster star in films like Trading Places and Beverly Hills Cop. Murphy came up with the film’s “a playboy gets his comeuppance” premise and brought on his frequent collaborators Barry W. Blaustein and David Sheffield to write the script. Murphy also recruited director Reginald Hudlin based on the strength of Hudlin’s debut feature, House Party. Despite Murphy’s stardom, getting the film made wasn’t without its uphill battles. Hudlin recalls a racist studio exec saying, “I don’t know how you’re going to make this work. I mean, Eddie Murphy in a romantic comedy? He’s got that broad nose and big lips.” Yet Hudlin had always been interested in placing black characters in genres they weren’t typically seen in. The affably goofy House Party was modeled after teen films like American Graffiti and Risky Business. For Boomerang, Hudlin cited Woody Allen and Preston Sturges as inspirations.

Boomerang holds a unique place in the rom-com pantheon. Like a lot of rom-coms with all-black casts, it’s often considered a “black movie” rather than a mainstream romantic comedy. That’s allowed it to become a beloved classic for some and a forgotten relic for others—as Gabrielle Union pointedly noted when Entertainment Weekly published a retrospective praising the film but referring to it as “underrated.” As Hudlin told FKB Online, “So many people love the film, from Lena Horne to Ice Cube. There are people who watch it with their family every Thanksgiving.” Shadow And Act argued, “Boomerang is not just a film, it’s a cultural icon and part of the black American collective consciousness.” And the Black Men Can’t Jump In Hollywood podcast released a wonderfully effusive episode about the movie, too.

Boomerang is beloved enough that BET recently debuted a sequel TV series executive-produced by Lena Waithe and Halle Berry herself. On the other hand, it definitely hasn’t enjoyed the broad mainstream cultural staying power of other early ’90s rom-coms like Sleepless In Seattle and Four Weddings And A Funeral. Which is especially weird because it was actually a big financial hit. Boomerang was one of the top 20 highest-grossing movies of the year, making $70 million domestically and $131 million worldwide. Yet coupled with mixed reviews and the fact that Murphy comedies generally delivered much bigger box office returns, it was somehow saddled with the reputation of being an unmemorable failure, becoming what The Dissolve would later term a “Forgotbuster.”

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Boomerang is well worth seeking out, either for the first time or a revisit. Aesthetically, Hudlin emphasizes the aspirational coolness of the world of powerful black professionals. So while the film definitely feels rooted in the time and place of the early 1990s, it doesn’t look unpleasantly dated—an impressive trick to pull off. There’s a particularly memorable Thanksgiving sequence that features not just John Witherspoon delivering a hilarious monologue about his mushroom-related sartorial choices, but also Murphy and Berry decked out in jumpsuits that would still look breathtakingly chic today.

For those who are discovering Boomerang for the first time, one thing to note is that it gets better as it goes along. The first act is the film’s most uneven, with a broader comedic style that doesn’t reflect the sensitive, nuanced rom-com the film ultimately becomes. Like a lot of pop culture from the era, there’s a strain of casual “comedic” transphobia and homophobia that feels especially jarring when it’s central to the very first scene between Marcus and his friends Tyler (Martin Lawrence) and Gerard (David Alan Grier). The film eventually settles into a fun Sex And The City dynamic wherein the trio offer three different perspectives on contemporary dating life, with Gerard as the hapless romantic, Tyler as the crass know-it-all, and Marcus somewhere in the middle. But it’s not immediately clear that Tyler’s most outrageous opinions are there to be challenged by his friends—even if there is a satisfying early moment where he complains that “bitches” never randomly flirt with him, to which Marcus deadpans, “Maybe it’s because you call them bitches.”

Perhaps to compensate for Murphy’s toned-down demeanor, the film demands really over-the-top performances from Eartha Kitt and Grace Jones as the eccentric public faces of the cosmetics company that merges with Marcus’ company and brings Jacqueline into his orbit. Comedy is particularly subjective, of course, so maybe there are those who find the image of Grace Jones taking off her underwear and wiping them in a coworker’s face while yelling, “This is the essence of sex!” funnier than I do. (You certainly can’t find fault with Kitt and Jones’ willingness to throw themselves into these self-mocking roles.) But overall, the film’s opening act has a weird, unpleasant undertone of, “It’s funny when men are sexually harassed at work because usually women are the ones sexually harassed at work!”

For me at least, the film doesn’t become an unimpeachable rom-com masterpiece until about halfway through. That’s when it moves away from broad, rather retrograde comedy about gender politics to become a much more nuanced story about Marcus’ emotional journey. His confidence is shattered when Jacqueline starts treating him in the manipulative, disposable way he’s long treated his romantic conquests. And with his focus squarely on winning Jacqueline’s heart, Marcus is able to develop an actual friendship with Angela, which lends the film a When Harry Met Sally tension to complement its central battle-of-the-sexes premise.

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There’s definitely stuff to like in the film’s more heightened first half—particularly Tisha Campbell as Marcus’ irate neighbor/former fling and Chris Rock in a tiny, scene-stealing role as Marcus’ friend from the mailroom. (As Hudlin presciently observed on set, “One day people are gonna look back and they won’t believe all these people were in the same movie.”) But the second half is where Boomerang truly shines, thanks especially to Berry’s radiantly watchable performance and the warm chemistry she has with Murphy. Although she’s framed as a sort of ideal “girl next door,” the film smartly gives Angela a real backbone, too, including a powerful moment that inspired the Toni Braxton single “Love Shoulda Brought You Home.” (The film’s killer R&B soundtrack eventually went triple-platinum.) Like the best rom-coms, Boomerang also gives Marcus an arc beyond his romantic one. The film offers a sneakily great friendship story, with David Alan Grier turning in a particularly wonderful performance as the openhearted friend Marcus takes for granted.

In a lot of ways, Boomerang feels really ahead of its time, with a heightened tone and workplace-centric structure I associate way more with rom-coms of the early 2000s than the ones released right at the start of the rom-com renaissance. Yet it still captures the best of ’90s romantic comedy naturalism. Reviews of the film tended to focus more on the negative than the positive, however, and—as is so often the case when it comes to mixed reviews of films about underrepresented groups—it’s impossible to say how much of that reaction was influenced by unconscious social bias. (The film actually acknowledges that maddening reality in a funny, pointed runner in which Tyler is constantly trying to suss out which small interactions and elements of society are based on subtle ingrained racism—like the fact that a game of pool ends when a white ball drives a black one off the table.)

For his part, Murphy was frustrated enough with the critical reaction that he published an impassioned 1992 op-ed in the Los Angeles Times, calling out reviewers who had dismissed the film’s world of upper-middle-class black professional life as something fundamentally unrealistic or fantastical. He also defended the authenticity of a scene where Marcus and his wealthy black friends are racially profiled in a clothing store, eventually noting, “I cannot be more passionate when I say that the situations found in this film are not from some fictional dream world. Until everyone can realize this, the cancerous roots of racism will continue to spread, and the people of this country will continue to be torn apart and destroyed by the disease of misunderstanding.”

Murphy also discussed the backlash on a 1992 Tonight Show appearance. After Jay Leno notes there’s likely a cultural bias because people aren’t used to seeing black actors in these types of roles, Murphy responds confidently, “Well, you better get used to it because I ain’t going no place.”

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That statement turned out to be true in the sense that the 1990s and 2000s brought Murphy continued cultural ubiquity in a string of major box office hits. But artistically speaking, his performance in Boomerang feels more like an outlier than the start of something new. As Hudlin put it years later when asked about why the film’s financial success didn’t inspire a wave of other rom-coms with black casts:

That was one of the tragic circumstances. We thought this movie would start a chain of films like this and it didn’t. There was this real hostile reaction in certain corners in Hollywood to the film. Eddie wasn’t doing what Eddie was supposed to do, which is to be a fast talking con man. It was him evolving his image… At the time, there was a negative pushback in mainstream Hollywood to the notion and prospect of what Boomerang represented.

Indeed, though some critics, including Roger Ebert, praised Murphy’s shift in performance style, there was definitely a trend of reviews expressing frustration at what they felt was Murphy’s vanity-driven attempt to manage his public image.

With the benefit of hindsight, Murphy’s low-key performance in Boomerang looks like a revelation and a bittersweet glimpse at a path not taken. “Aw man, I just look really comfortable in my own skin in this movie,” Murphy told Hudlin when shown the film for the first time. Perhaps it’s too neat to point to Boomerang as a sort of “Rosebud” moment in Murphy’s career. But especially given how personally Murphy seemed to take criticism of the film, you do have to wonder if his career might have unfolded differently if his out-of-the-box work in Boomerang had been more universally embraced. Like his Oscar-nominated turn in Dreamgirls or his strong work in the otherwise abysmal Mr. Church, Boomerang is a reminder that Murphy’s talent is far more multidimensional than his film career often demonstrates. Now that the rom-com genre is having a cultural comeback, perhaps it’s time for Murphy to put those skills to good use again.

Next time: 10 Things I Hate About You turns 20.