It’s often much more difficult to evaluate a screenwriter’s career than that of a director or an actor. Sure, movies are always collaborative—the actor hopes the director and editor choose good takes, the director hopes the producer doesn’t insist on modifying their vision, etc, etc—but the screenwriter is often the one who has done the most to begin shaping the film, and has the least control over what their contribution ends up looking like. Most screenwriters end up less known to the public than their directing counterparts; it is also uniquely possible to make a living at screenwriting and never see any of your sold scripts actually hit the screen.

But there are those screenwriters who have cultivated an image, whose names are known and bring up an association: the dark adventures of David S. Goyer; the topical dialogue-playgrounds of Aaron Sorkin; the focused biopics of Dustin Lance Black; the feminist-tinged pop culture commentaries of Diablo Cody. And though she’s not yet as known a name as those I just mentioned, screenwriter Aline Brosh McKenna has done a fine job of building up her own brand: first with romantic comedies, adding a more recent shift to focusing on the balance between work and personal life for a central female character. It’s been a bit of a bumpy road, though. With a couple of big hits in her past, a high-profile recent failure, and an interesting collaboration with a well-known director that debuts tomorrow, I’ve been pondering her career trajectory.

First, that failure. After a seemingly endless, everywhere-you-turned publicity campaign for the new Sarah Jessica Parker film I Don’t Know How She Does It, which McKenna scripted from the novel by Allison Pearson, the film opened this past September to numbers that were surely a crashing disappointment for its studio: just $4.4 million on 2,476 screens its opening weekend, to land in sixth place. The final box office take was under $9.7 million, on a production budget of $24 million. (All figures are for U.S. box office and taken from Box Office Mojo, one of the greatest sites on the internet.) There are a lot of angles from which to examine this failure: whether Parker is actually a credible movie star; whether the marketing hit the right note for a “women’s picture”; whether women even want to see these kinds of stories at all. It’s that last bit that interests me the most. (I have not seen this film yet; the reviews were not favorable.) McKenna had written or co-written five other films that aim for a similar audience before I Don’t Know How She Does It, some of which have seen much more success than others, one of which saw a brush with awards contention, a major component of the careers of all of the screenwriters listed above. What has seen financial success, and what hasn’t? (I’m speaking strictly in this case about domestic box office returns, understanding that films make much of their revenue from other sources.) What have women—and at least a few men, presumably—gone to see in the theater?

McKenna’s first produced film screenplay was for the Matthew Perry-Neve Campbell-Dylan McDermott love triangle film Three to Tango (1999); she co-wrote from a story by Rodney Patrick Vaccaro. I remember seeing this film in the theater and really liking it…but of course, I was 16 then, and didn’t have nearly as good of taste as I thought I did. (Will my 40-year-old self say the same thing about today-me in another dozen years? I hope not.) Having re-watched it recently, it is so very, very, very late ’90s in the worst possible way, that I’m not sure it’s possible to objectively critique with my current level of cynicism. Squealing, Mighty Mighty Bosstones-esque music for “comic” scene transitions! “Not-that-there’s-anything-wrong-with-that”-style hijinx, as Neve Campbell thinks Matthew Perry is gay! That cast, that cast. It’s always a little hard to blame something for being a product of its time, but the parade of mediocrity on display here is still worth noting. The film didn’t find much of an audience, grossing a bit under $10.6 million domestically, just over half of its $20 million production budget.

After Three to Tango, McKenna’s next film credit is the 2004 romantic comedy Laws of Attraction, starring Julianne Moore and Pierce Brosnan. The film was a box office flop, grossing about $17.9 million domestically, which was only a little over half of its $32 million production budget. It is also highly ridiculous, perhaps more so than Three to Tango, with the two actors playing divorce lawyers who square off in court and deal with sexual tension out of it…before a drunken escapade that leads to them marrying each other and dealing with the fallout. McKenna co-wrote this screenplay with Robert Harling and is credited with the story, which shows little of the finesse of her next film.

>Easily the biggest financial hit bearing McKenna’s name, the 2006 novel adaptation The Devil Wears Prada grossed almost $125 million domestically on a production budget of $35 million. The film also garnered far more accolades than McKenna’s previous projects, including an Oscar nomination for Meryl Streep and a BAFTA nomination for McKenna for best adapted screenplay. Here is where she seems to step into her own: the film has a romantic element for its heroine, of course, but the core dilemma is about her career. The success of The Devil Wears Prada (both the novel and the film) would seem to show that when these elements are combined in a satisfying and fun way that takes the central character seriously, the audience is there.

Two years later, 27 Dresses was the first film that’s screenplay is credited as an original work by McKenna alone. Directed by Anne Fletcher, the film starred Katherine Heigl as the always-always-always a bridesmaid Jane. The film was a genuine hit, grossing $76.8 million domestically on a $30 million budget, but in my personal opinion is not nearly as good a film as The Devil Wears Prada. Its heroine’s workplace dilemma is…she’s in love with her boss (groan). McKenna herself has said, in an interesting profile in The New York Times before I Don’t Know How She Does It came out, that she finds writing traditional romantic comedies to be quite difficult, and I think it shows here. The film has very little originality. However, McKenna’s next film, which follows some of the rhythms of a romantic comedy but focuses very much on the heroine’s work situation, is in my opinion her strongest.

I gave 2010′s Morning Glory a positive review when it was in theaters, and have since watched and praised it again. The film deserved to do much better than the $31 million it earned domestically (off of a $40 million production budget), and coming off of the previous two financial successes of McKenna’s career, its lackluster performance perplexes me. It’s a solid, funny film filled with recognizable and charming actors (Rachel McAdams, Diane Keaton, Harrison Ford), marketed as from the writer of The Devil Wears Prada and the director of Notting Hill (Roger Michell), and offers something that does not talk down to its target audience, as so many films “made for women” do. (For the record, this film is very much rounded enough to appeal to men, as well.) No wonder film studios so often seem unable to tell what will or won’t be a hit; from my perspective, this one is a mystery.

McKenna’s next chance at a hit starts tomorrow. Unfortunately, it seems that maybe what looked like her second shot at something close to a prestige film—after The Devil Wears Prada—isn’t getting the buzz one would hope for. Cameron Crowe’s We Bought a Zoo, starring Matt Damon, Scarlett Johansson, and Elle Fanning, didn’t get many hopes up with the trailer, and on the eve of its release, I’m not hearing too much anticipation. (McKenna and Crowe are each credited on the screenplay, adapted from the memoir by Benjamin Mee.) In fact, this writer’s Twitter feed has even been filled with lots of merry jokesters having fun with the film’s goofy premise and title. And, in a holiday season that has seen many family-friendly films underperforming at the box office, hopes are not bolstered. I will be interested to see how the numbers end up.

Still, no matter the performance of We Bought a Zoo, it’s clear that McKenna is here to stay for a while. She built a name writing the kinds of movies that women are more easily allowed to use to break into the business, and is now branching out without betraying her brand. It was a savvy strategy, and I believe she has a lot of potential to contribute to quality films in the future. I will continue to watch for her involvement in projects, and encourage people to watch Morning Glory (seriously…it’s streaming on Netflix right now).