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With an apparent change in selection criteria, Paltrow's head lost out to her heart for the next couple of films, Duets and Bounce. No one could really blame her motivation for doing Duets, as it was her chance to be directed by her father, Bruce Paltrow, who would pass away from throat cancer two years later. Despite being an ensemble road trip/drama/musical film, Bruce's little girl was far and away the most recognizable name in the cast, unless this was 1985 and Huey Lewis was still all the rage or you were a huge "Felicity" fan. So, the paltry box office for this Paltrow project of $4.7 million against a reported $16 million budget showed that a departure from the serious, important films might not be the best idea at the time. It also did no one involved any favors that Duets was ravaged by critics, with RottenTomatoes showing that the movie received only a 22% Fresh rating. Clearly, this sentimental project was bona fide misstep.

Two months later, Paltrow re-teamed with Shakespeare in Love co-star and then-boyfriend Ben Affleck for the romantic drama Bounce. If you are like me, I tend to even forget that Affleck was in Shakespeare in Love. I'm not sure what that says about him or his role. Anyway, Bounce was a co-headlining film with both Affleck and Paltrow sharing considerable screen time together and it didn't exactly have blockbuster written all over it. The film's plot centers on Paltrow as a widow, whose husband was on board a plane that crashed because Affleck's character gave him his seat. Guilt and its apparent, unlikely byproduct, flirtation, ensue and the movie doesn't really go anywhere, which is very much like the similarly-themed and equally-uneventful but much more salacious Random Hearts from the year before. With an opening weekend of $11.4 million, a light bulb should have gone off in the studios' heads that neither of these actors are big-time draws outside tentpoles, which open big regardless, and Oscar bait, which typically have the slow build. Fortunately for Miramax (Harvey Weinstein must be Paltrow's bookie since she was their stable actor), Bounce would virtually break even with a $36.8 million gross against a modest budget of $35 million.

So far, Oscar hadn't led anywhere particularly glamorous or profitable for Paltrow. She was making her own choices for her own reasons and not because she had Oscar in tow.

Following another side trip into indie ensemble territory, by appearing in Alan Cummings and Jennifer Jason Leigh's The Anniversary Party, Paltrow attempted her most mainstream and uncharacteristic film yet – the Farrelly brothers' Shallow Hal in November 2001. That's right. The queen of Miramax's Oscar canon teamed up with the reigning court jesters, donning a fat suit to boot. To draw the parallel to high school, Paltrow basically left her comfort zone of the theater kids for the slacker dudes hanging out behind the cafeteria smoking a bowl before skipping P.E. for a munchies run. With Shallow Hal, Jack Black was trying to parlay his hysterical supporting role in High Fidelity into lead roles. Paltrow is the object of the title character's attention and carries the heft of the comedy.

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