9. Sleepless in Seattle (1993)
As sappy and predictable as it is, Sleepless in Seattle is richly entertaining and justifiably sentimental. It is a celebration of some of the great, dazzling romances of Hollywood’s past, including An Affair to Remember, which this film directly references. With When Harry Met Sally…
Nora Ephron had already shown her ability to tell a convincing and endearing love story, but here she also demonstrates her prowess as a director. Even when the plot is extraordinarily implausible, it is hard to not find yourself rooting for the two leads to find sanctuary in each other. Sleepless in Seattle uses the charm and intelligence of its cast to its advantage, and it works as a corny and enjoyable date movie.
10. Jerry Maguire (1996)
In true Cameron Crowe fashion, this movie offers countless quotable lines of dialogue wrapped around a resounding love story. As the events of the movie play out, the audience is shown the wonders that can be found in various outlooks on life. While Jerry is initially punished for his ethical insights, he is able to ascend the path to redemption.
Tom Cruise creates some of his most convincing scenes to date as the title role, as he uses his maniacal disposition to highlight the character’s fall into an absolute breakdown. Jerry Maguire may be just a little lengthy for what it is, but each scene adds to the tinges of humanity within the commanding performances and the concrete screenplay.
11. Chasing Amy (1997)
Here’s a film that could only be made in the 1990’s , when people were finally willing to have an open discussion about homosexuality but there weren’t yet rules in place as to how to so with sensitivity. While the male and female leads do have great chemistry with one another, the sturdier bond is definitely between Ben Affleck and Jason Lee. As roommates/best friends/business partners, the pair sells the idea that they have a powerful relationship.
Chasing Amy shows some of Kevin Smith’s most introspective writing, as he examines the motivation (selfish or otherwise) people have when pursuing romantic partners. The level of insight into which this film approaches sexuality, love, and friendship is surprising only because it comes hidden in a slacker comedy. The dialogue in this movie is a perfect mixture of biting and believable, creating a realistic portrait of these characters’ lives.
12. My Best Friend’s Wedding (1997)
From the opening credits, the tone is set by the ideas of love that are present throughout pop songs of the 1960’s. My Best Friend’s Wedding aims to celebrate the vision of love that is created by these tunes, but it also combats their logic and reliability. The outrageous scenes that comprise this movie disregard any hope for believability in favor of entertaining storytelling.
Julia Roberts’s character fumbles from the sophistication of her life as a critic to a level of irrational delusion when she realizes that what she actually craves has been at arm’s length for years. While this may seem like an unlikely character transformation, most people who have had an encounter with romantic love can tell you that it doesn’t breed rationality. While the movie can be over the top and predictable, it gives rise to soulful performances and a satisfying resolution.
13. As Good as It Gets (1997)
In the first role that truly portrayed him as an aging man, Jack Nicholson plays a neurotic writer whose reclusiveness and lack of social intelligence limit his ability to form lasting connections with others. His ego leads to a complete dismissal of any other people he encounters. That is, of course, until he meets Helen Hunt’s snarky waitress. As Good as It Gets is a witty and touching comedy with smooth dialogue and authentic characters.
The acting in this movie is reserved but passionate, which was validated further when both of the leads took home Oscars for their performances. This film has all of the emotion of the classic romances that it clearly respects, while bringing in the nuances and standards prevalent at the end of the 20th century. As Good as It Gets is only strengthened by repeat viewings.
14. High Fidelity (2000)
In what effectively turns out to be a sultry love letter to both the dying medium of vinyl and the illustrious city of Chicago, this adaptation of Nick Hornby’s novel examines the relationship between an obsessive appreciation for art and a disillusioned removal from reality.
As the compulsive and idiosyncratic record store owner Rob Gordon, John Cusack gives one of his most expressive performances, while he is somehow able to capture the character’s complex blend of self-deprecating humor and misplaced arrogance.
Each track on the skillfully crafted soundtrack adds to the atmosphere surrounding a man who is only able to experience the world through music, as distorted as his view of it may be. As Rob walks us through his romantic past, we are forced to wonder whether or not we side with him, but even at his least likeable he is painfully relatable. He doesn’t need to break the fourth wall to gain our interest in his story, but it sure helps.
15. Love Actually (2003)
With a cast comprised of seemingly every celebrity the United Kingdom had to offer at the time, Love Actually manages to make what would normally be a story bloated with characters and subplots work on a level that is both insightful and engaging. Because each of the stories has a limited amount of air time, the focus is placed on the essentials, rather than stretching out one romance to fit its running time.
This film plays out like the best kind of drugstore short story collection, and the ways in which the tales are intertwined never seems forced even at their most ridiculous. While the movie is firmly steeped in romance, it also explores the other types of love, as we see the complicated bonds of familial relationships. Love Actually isn’t grounded in reality, but its charm allows it to become handsomely optimistic and shamelessly entertaining.
16. Knocked Up (2007)
Much of the memorable comedy from the first decade of this century was created in part by Judd Apatow. In Knocked Up, he offers an original take on the difficulties of modern dating and the implications of unplanned pregnancy. Following Apatow’s other works, this movie uses crude humor to open up more serious discussions.
What makes it most endearing is that it never shows Katherine Heigl’s character as a victim of circumstance; even as she battles all of the hardships of pregnancy and the struggle to balance them with her professional life, she is a strong, adept woman who is able to fight for a life that undertakes all of her goals.
Even the minor characters are compelling – particularly the couple played by Leslie Mann and Paul Rudd, which is probably why they got their own spin off movie a few years after this one. The natural and realistic feel to the majority of this film allows it to be charismatic while also defying some of the conventions of romantic comedies.
17. Forgetting Sarah Marshall (2008)
In what is one of the most faithful representations of a breakup on screen, Jason Segel demonstrates his prowess as both a comedic actor and a sharp writer. There is significantly more depth to this picture than you would normally expect from a movie like this. Segel’s character is plummeted into despair after his longtime girlfriend walks out, only to bump into her at the resort he travels to in the hopes of finding seclusion and recovery.
Forgetting Sarah Marshall is able to use its raunchy absurdity to flip expectations of the genre, such as the brief full frontal nudity which is only performed by males. It is a movie about forgiveness, complete with all of the self-destruction that sometimes goes into the process. Even the characters who display the most disgusting behavior are capable (and worthy) of attaining redemption.