Jennifer Lopez’s Best Comedy Movies, Ranked

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Can you believe The Wedding Planner, the 2001 rom-com starring Jennifer Lopez and Matthew McConaughey, is 20 years old? That’s right: As of Tuesday, January 26, The Wedding Planner is old enough to go to college. Directed by Adam ShankmanThe Wedding Planner introduces us to Mary Fiore (Lopez), a top-notch San Francisco wedding planner with a keen attention to detail and a strong ambitious streak. Mary is so good at her job that she has turned the art of getting married into a science despite leading a very single, lonely life. Everything changes for this star wedding planner when a chance encounter with a handsome doctor named Steve (McConaughey) leaves Mary romantically drawn to him despite the fact that he just so happens to be one-half of her newest wedding assignment.

Below, we’re ranking Lopez’s live-action rom-coms — as well as her comedies and romances — to celebrate the milestone anniversary of one of her biggest and most popular movies to date. Lopez has carved out a varied and intriguing niche in the lighter side of entertainment and always delivers attention-grabbing, memorable performances. So, given the variety of rom-coms, comedies, and romances she’s starred in to date, we figured it was high time we seized on the chance to rank them in honor of The Wedding Planner‘s big anniversary.

11. Gigli

Image via Columbia Pictures

Gigli is on this list because it technically and theoretically is, to varying degrees, a comedy and a romance. But Gigli is also a major black spot on Lopez’s resumé and, even worse, the second movie where Ben Affleck plays a man attempting to convince a lesbian to love him. So we don’t really need to intellectualize why it’s at the bottom of this list, do we?

10. Jersey Girl

Image via Miramax

Now here’s a Bennifer-era movie I can get behind. Jersey Girl is a unique entry for Lopez in that it’s probably the one role where her screentime is remarkably diminished at a period in her career where she was a bonafide star. Lopez appears in a handful of the opening scenes of Kevin Smith‘s 2004 movie (and his fifth collaboration with Ben Affleck by this point in time). Lopez is doomed to be the fridged wife of high-profile publicist Ollie (Affleck) and mother of Gertie (Raquel Castro). She and Affleck have compelling chemistry as a couple in the movie’s early establishing scenes, which may be down to the fact their real-life chemistry as a couple is bolstering their performances. But we don’t get much of Lopez since her character, also named Gertie (the single worst character name of any Lopez character to date), dies in childbirth and sets off the chain of events we see for the rest of the movie. So, props for the solid and reliable near-cameo, Lopez, but this is as far as Jersey Girl goes.

9. The Back-Up Plan

Image via CBS Films

The Back-Up Plan is a low point for Lopez, a point where the roles she took on actively factored into the equation that she was in her 40s and centered a majority of character development around this fact. In the case of The Back-Up Plan, Lopez plays Zoe, a 40-something single woman who still has not found “the one” and decides to conceive through artificial insemination so she can finally start the family she’s always wanted to have. The big twist here is that Zoe finally meets “the one” — a cheese monger named Stan (the single worst character name of any character Alex O’Loughlin has played to date) — around the time she finally gets pregnant. Despite Lopez’s best efforts, The Back-Up Plan cannot tap into the kind of bouncy, kinetic energy of the actor’s rom-coms and comedies from just a decade before. This is also a movie that doesn’t quite know how to deal with Lopez not being in her 20s anymore and just turns her age and the circumstances of her character’s pregnancy into weird punchlines that feel absurdly male and regressive. Lopez deserved better than this.

8. Shall We Dance?

Image via Miramax

Lopez and Richard Gere? Sign me up. A remake of a Japanese feature of the same name, Shall We Dance? follows a lawyer (Gere) with a pleasant and stable home life who still feels like something is missing. He decides to mix it up when he finds himself in the dance studio of a skilled ballroom instructor (Lopez). Shall We Dance? is the rare Lopez movie where we’re reminded that when she’s not acting, she’s singing and dancing for the masses because her performance here requires she put those dancing skills to good use. But as good as Lopez gives in Shall We Dance?, she is mostly saddled with a crummy character arc as the beautiful and mysterious Paulina, a woman whose life has a black cloud hanging over it because she lost a prestigious dance competition the year before. I don’t doubt something like that can be a blow to a person, but it forces Lopez to play a character who is aloof and occasionally brusque — qualities that do not gel with Lopez’s frequently sunny and warm onscreen personality.

7. Jack

Image via Buena Vista Pictures

Don’t knock Jack until you’ve revisited. Arguably the wildest entry on director Francis Ford Coppola‘s resumé but definitely the kind of movie you’d expect to see Lopez pop up, Jack tells the story of Jack (Robin Williams) a young boy who is born with a rare condition which physically makes him appear to be a fully-grown man. For my money, Jack is tender and sweet coming-of-age story about a character who has, in some ways, already come of age. Lopez plays Miss Marquez, Jack’s grade school teacher who helps Jack acclimatize to school after years spent at home in a safe bubble created by his parents. Lopez is so warm and kind and brings real sympathy to this high-concept story. Even though she only occupies a supporting role here, Lopez makes the most of her part and shows us what she can do when the role she is given suits her and she is able to put her whole heart into it.

6. Monster-in-Law

Image via New Line Cinema

I have a soft spot for Monster-in-Law, but not too soft that I don’t realize it’s a hot mess of a movie. In Monster-in-Law, Lopez plays Charlie, an aspiring fashion designer holding down multiple temp jobs to make ends meet. Charlie meets a successful doctor named Kevin (Michael Vartan) while catering an event and the two hit it off. When the time comes for Kevin to introduce Charlie to his mother, it’s revealed she is none other than award-winning, high-profile journalist Viola Fields (Jane Fonda). Unfortunately for Charlie, Viola is overly protective of her son and makes it her sole mission to break the young couple up as they plan their wedding. Now, Monster-in-Law ranks so high in this list because it is probably the only time we will get to enjoy a Lopez-Fonda onscreen sparring match and it’s actually not a terrible comedy. Lopez is undoubtedly second banana to Fonda, who is in the midst of a career renaissance with this role at this point after being offscreen for over a decade. But Lopez manages to keep pace with Fonda and make some of the movie’s more over-the-top moments, like Charlie sustaining a severe allergic reaction which forces Lopez to do physical comedy (not her strong suit), feel believable.

5. Second Act

Image via STX Entertainment

Lopez shines in Second Act and gives the movie more of a credibility boost than it deserves. The last decade for Lopez has proven to be more uneven than we might expect from a star of her caliber at this stage in her life and career. As such, from the outside it would seem like Lopez has become more careful about the roles she signs on for — something she also has the luxury of doing now that she is an A-lister and audience favorite. The fact that Lopez signed on for Second Act shouldn’t come as a surprise, when you keep all of this in mind, because it’s exactly the kind of movie that is a sweet spot for Lopez. No matter how big Lopez has gotten over the years, she has always, always, always worked well when playing relatable, working class heroes who can transcend unbelievable circumstances and bring some real life to the screen. In Second Act, Lopez plays Maya, an employee at a big box store who has proven she has the stuff for a corporate role but is passed over. Maya’s efforts to claim what she has rightfully worked for land her a plum role at a cosmetics company, where her presence allows her to put her talents to good use and livens up the rest of the company. The role is a relative walk in the park for Lopez and there are some plot twists in this 2018 movie that are actually bananas (including one involving Lopez’s co-star Vanessa Hudgens), but Second Act is a proof that Lopez still has what it takes to turn a so-so movie into a winning feature.

4. Out of Sight

Image via Universal Pictures

The one-two punch of Selena in 1997 and Out of Sight in 1998 is what legitimizes Lopez as an actor. It is also, by this point in her career, one of the more creatively bold and artistically challenging roles Lopez has managed to snag. As U.S. Marshal Karen Sisco, Lopez shines in this Steven Soderbergh-directed feature. Out of Sight is more of a crime comedy, with the story following Karen as she and career criminal Jack Foley (George Clooney) find their lives entwined in a twisty cat-and-mouse pursuit. Lopez’s chemistry with Clooney is off the charts, making this one of her most exciting performances to watch to this day. And while this is also one of the most prestigious movies Lopez has performed in, I’m putting it at #4 because it is a comedy which relies heavily on crime thriller plot mechanics and risks pulling focus from the reason we’re all here, ranking Lopez’s rom-coms.

3. What to Expect When You’re Expecting

Image via Lionsgate

There is a lot that is not so good about the ensemble comedy What to Expect When You’re Expecting, but Lopez is one of the few things that is so right. Lopez plays Holly, an Atlanta-based photographer who is dying to have a child with her husband, Alex (Rodrigo Santoro). While Holly is keen to bring a child into their lives, Alex, a former musician with some of that free spirit still intact, is hesitant. Despite Lopez shouldering a smaller role in this bursting-at-the-seams starry comedy, her performance is a great reminder of how utterly magnetic she can be when she is onscreen. Lopez makes sure Holly stabilizes What to Expect and turns the character into a realistic, soulful human being whose desires to become a mom feel real. Where What to Expect spends its time spinning its wheels on some of the goofier storylines (I’m looking at you, Cameron Diaz), the movie has the good sense to give Lopez a meatier arc with legitimate stakes and pair her with Santoro, arguably the most handsome co-star she’s had in any comedy thus far.

2. Maid in Manhattan

Image via Columbia Pictures

Maid in Manhattan is Lopez’s big rom-com follow-up to The Wedding Planner and features a similarly strong performance. Lopez is once again in the pocket in this 2002 as Marisa Ventura, a maid at the Beresford Hotel and a single mother. Marisa’s life is turned upside down when she is mistaken for a socialite by senatorial candidate Chris Marshall (Ralph Fiennes). Chris is smitten and so is Marisa, so she pretends to be someone she’s not while dating Chris. Directed by Wayne Wang (The Joy Luck Club) and based on a story written by The Breakfast Club scribe John Hughes under a pseudonym, Maid in Manhattan contains a sincere performance from Lopez. This is a movie which contains some intriguing and realistic depictions of how race and class could affect a classically charming rom-com couple — something Lope and Fiennes navigate masterfully as the respectively expert actors that they are. But Maid in Manhattan comes second to The Wedding Planner if only because Lopez and Fiennes don’t quite sell us with their chemistry, which is a necessary component of a rom-com.

1. The Wedding Planner

Image via Columbia Pictures

This is it, the top of the top, the cream of the crop. By far the best comedy — or romantic comedy, for that matter — that Lopez has starred in to date is the reason we’re here to celebrate her work. The Wedding Planner is still a winning rom-com and one of Lopez’s best roles after 20 years. Under Shankman’s confident direction, Lopez turns in a charming, layered, sympathetic performance that helps ground the wilder setpieces and more unbelievable (but necessary since it’s a rom-com, after all) narrative twists, like a childhood friend now asking for her hands in marriage or removing a statue’s manhood from Steve’s hand after it gets stuck. The Wedding Planner is a major turning point for Lopez, too. After a decade of mostly supporting roles, The Wedding Planner allowed Lopez the opportunity to prove she can lead a movie and make it a box office winner. Today, The Wedding Planner is one of the best rom-coms of the early ’00s rom-com boom, with Lopez coming out on top as a confirmed star who can make magic onscreen with any one of her co-stars.

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