Guess Who with Zoe SaldanaIn Guess Who, a race-reversing remake of Guess Who’s Coming to Dinner?, Kutcher tried to win over the family of his black girlfriend, played by future Avatar star Zoe Saldana, including her hard-to-please father, played by the late Bernie Mac. Verdict: A little frayed, but with potential 
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No Strings Attached with Natalie Portman In No Strings Attached, Natalie Portman plays a commitment-phobic doctor who starts a strictly-sex relationship with her TV production assistant pal, played by Ashton Kutcher
A Lot Like Love with Amanda Peet In A Lot Like Love, Kutcher stars opposite Amanda Peet as two twenty something singles who slowly fall in love through numerous, brief interactions over the course of several years. Verdict Hanging on by a thread.
Contrary to that notion, Emma’s greatest challenge and obstacle is not falling in love
What Happens in Vegas with Cameron DiazKutcher took the plunge again in 2008’s What Happens in Vegas, accidentally eron Diaz after a drunken night in Sin Cityplicating matters, after their night of debauchery, the newlyweds win the slot machine jackpot, leading each of them to spend the rest of the movie trying to do away with the marriage and keep all of the money. Ah, romance. Verdict: She’s stringing him along we think.
Killers with Katherine HeiglIn the action-comedy Killers, Kutcher joined forces with Katherine Heigl to play a suburban married couple whose domestic bliss is interrupted by Heigl’s character’s realization that her husband is a trained assassin, and himself the target of a hit. Verdict: Too many knots to untangle.
Instead, the premise of the film felt like an opportunity to explore an idea that (on paper, at least) seems like a logical and perhaps even an ideal arrangement. The screenwriter even confesses, “This movie is a bit of wish fulfillment for me-the idea that you could sit down and agree that you’re only going to have a physical relationship and if anything else develops, you can abandon ship.”
Emma is a unique character in the traditional romantic comedy genre, where the female protagonist often has the sole goal of finding Mr. Right and getting married. “Emma is a doctor who isn’t looking for a relationship. She has an aversion to attachment, because she has a hard time losing people,” explains Natalie Portman.
It is such customary romantic comedy moments viewed through Ivan Reitman and Elizabeth Meriwether’s topsy-turvy looking glass that give the leads ample opportunities to generate laughs. The director is more than pleased with the results. Per Ivan Reitman, “I’m very proud of the cast of the film. I think certainly our two leads, Ashton Kutcher and Natalie Portman, are almost iconic representatives of their generation, people in their late 20s and early 30s. We’ve certainly seen Natalie Portman act in a lot of serious films, but we’ve not had the opportunity to see her let it rip in a comedy, but in a human and truthful way-that was what I really hoped to get with her, and I think she delivers in spades. With Ashton Kutcher, he’s more known for broader comedies and for the work that he’s done on television, and my desire was to put him in something where he got to really show what a thoughtful person and what a fine actor he really is. Again, he hits all the right chords beautifully.”
With the leads in place, Ivan Reitman set out to put together an ensemble cast that incorporated some of the best and brightest in the world of character comedy.
Working with the veteran director did not go unacknowledged by the young cast. “Ivan has made some of the most quintessential movies of my youth. I grew up watching ‘Ghostbusters’ and ‘Stripes’ and, along with all of those other comedy tent poles, they became pillars in my life,” says Ashton Kutcher. “Ivan is absolutely legendary in defini g a genre for a generation, and he’s still doing it.”
Just , Kutcher tested the tempestuous waters of romantic comedies, playing husband to his then real-life girlfriend, the late Brittany Murphy. In the film, Kutcher and Murphy’s Tom and Sarah marry after only a few months together and then suffer a disastrous honeymoon in Europe, during which they break up. But, as is often the case in romantic comedies, things ultimately work out for the central couple.Verdict: A bit stretch, but with some compromises they could survive.