25) A Room with a View (1985)

24) Pillow Talk (1959)/Down With Love (2003)

23) Chasing Amy (1997)

Above all else, Kevin Smith's Chasing Amy is an elegy for the foolish lover-- a lilting tune for those sad sacks that let a thing of beauty slip through their fingers for reasons even they cannot understand. It is a tragedy about three individuals caught in a maelstrom of emotions they cannot cope with, but also Smith's sharing of the intimate knowledge that with love there often comes loss and with loss there are often lessons to be learned about one's self and the life you will lead in the future. Chasing Amy came at a time when Smith was dejected with the Hollywood business model and, turning down several million dollars in budget, Smith made this often uncomfortable but bemusing movie of an authentic tale of love for a quarter of a million dollars and winds up with a deeply personal and soul baring film. Beneath its crude exterior of vulgar, sexually centered humor and buried within its despondent plot, a belief shines through that no matter the heartbreaking misery we so easily suffer by our own misguided hand, life goes on and the prospect of finding happiness is there if we can only accept our mistakes for what they were. Mistakes.

Chasing Amy is such an enterprising and resonant departure for Smith that even with the reoccurring characters and intertwining plot details between it and the other four films of his Jersey series, it stands as a much more grown-up undertaking. Though it is not his finest or even most profound film (That would be Dogma), it is the only one of his ventures where the comedy is secondary to the message, the characters, and romance presented. Chasing Amy is a romantic comedy in the sense that, yes, there are a lot of laughs as Holden (Ben Affleck) tries to woo Alyssa (Joey Lauren Adams). From that perspective Chasing Amy is a romantic comedy just as Clerks is a slacker comedy, Mallrats is a...well... action-slacker-romantic comedy, Dogma is a religious satire, and Jay and Silent Bob Strike Back is a hedonistic, fan favoring, spoof-heavy comedy adventure. But as we watch the romance take root, flourish, then wither, and eventually die, the laughs vanish like ghosts and the whole production begins to seem Shakespearean in nature-- just without all the bloodshed. We have two lovers uniting in an affront to some around them (though instead of using skin color or feuding families, Smith makes his female lead a lesbian); we watch jealousy rear its ugly head in both Holden and his best friend, Banky (Jason Lee); and Holden possesses a fatal flaw that brings about his downfall and the loss of that which he's worked so hard to achieve, that fatal flaw being a heavy dose of pride. 

If you have ever seen Kevin Smith out of character in any fashion (and if you have not then I would highly recommend the monstrously entertaining and insightful An Evening with Kevin Smith), you will know that he is generally a soft spoken, witty, but self-deprecating man that employs his crassness and sensitivity equally. The most difficult aspect of Chasing Amy is that after watching it once a second viewing becomes difficult, not only because it makes you mull over any past romantic injustices you've been a part of, but because it is an incredibly private look into the heart of Smith himself. His character, Silent Bob, is at his most loquacious in this film and delivers a reflective speech that not only gives the film its title and identifies Holden's pride, but comes off almost as Smith paying penance for his own past. It is a somber, but enlightening moment.

The characters start out in New York City. Holden McNeil and Banky Edwards, the creators of a popular comic book "Bluntman & Chronic", are guests at a comic book convention. After a near homicidal autograph session where Banky assaults an irritating collector demeaning Banky's status as "inker", the two gravitate towards a guest panel where minorities in the business speak about their place in comic books. It is there the only character more colorful than the sharp-tongued and homophobic cynic of Banky (who isn't as diabolical as the Bard's Iago, but who causes quite enough trouble as it is) is introduced in Hooper, the very effeminate homosexual black man that puts on a splendidly comic front as an angry, racially driven radical. After Holden and Banky participate in a staged argument on African Americans in pop culture and a fake shooting occurs to scare off the audience and panelists, the only person remaining is fellow comic book creator Alyssa Jones, who is unfazed by the shenanigans and amiably chastises the trio for their antics. Holden is immediately smitten with her and the four go to a bar where the two hit it off. These two early scenes are the high point of the film's comedy and the starting point of the air of romance throughout.

The affair is anything but generic. Holden soon finds out Alyssa is involved with another woman and he is forced to resign himself to being her friend only. The chemistry between the two is too powerful for them to handle though, and in a perfectly squirmy scene we wring our hands and bite our lip as Holden pours his heart out to Alyssa and pleads to give him a chance. Initially enraged at his sentiment, Alyssa comes to remember that the original reason she opened herself up to females was so that she wasn't cutting off fifty percent of the population in the search of her soul mate. She believes Holden might be that person and the two foster an all-too-perfect union. A dark cloud looms over them in the character of Banky, however. Banky harbors an incredible jealousy towards Alyssa, not only because of the chasm forming in his twenty year friendship with Holden, but because underneath the layers of gay jokes and machismo Banky might just be in love with his friend. He succeeds in digging up dirt on Alyssa and reveals to Holden a promiscuous past. When Alyssa admits the truth behind her youthful experimentation, Holden cannot accept the fact that his inexperience does not make him less of a man to her and that no matter her past, he is what she truly wants. And so come the heartbreaks and broken friendships as Holden confronts the two people closest to him about their secrets.

Smith tackles sensitive subjects (or at least what was considerably more sensitive eight years ago) like homosexuality and sexual freedom realistically and intelligently. Smith creates Banky as the lens through which the immature and ignorant would see these subjects, and frank monologues from Silent Bob (Smith's character), Alyssa, and Hooper (effectively Banky's foil) share with us viewpoints that would probably make the world a better place if they were more common. It is poor Holden, the everyman-- the every-dumb-conventional-thinkingman-- stuck in the middle and forced to learn things the hard way.

The cast of Chasing Amy is less important than the characters Smith has written to life. Jason Lee effortlessly upstages his co-stars with his energetic brooding and scathing commentary that cuts to the heart of matters, but it is the fact that his commentary is generally and terribly wrong that allows the viewer to pay more attention to Affleck and Adams. Note the way Banky says, "This is all going to end badly," early on. It's so subtle he probably doesn't even realize it, but he's not making a premonition. He's making a promise. Banky's bile exists because of problems he has with himself, not with the world, and when Banky declares with ostensible frustration that "man-friendly lesbians" are a figment of Holden's imagination, it feels like the desperate act of a spurned lover.

It is hard to see Chasing Amy as a great romance once the other shoe drops and the hurting begins. You might be asking right now how I could consider it so. Watch it. If Smith has it his way, by the end, you'll know.

22) Roman Holiday (1953)

If Ewan McGregor is one of the most charming, handsome, and romantic men ever to grace the big screen, then Audrey Hepburn is surely one of the most winsome, lovely, and romantic women to light up cinema. The elfin, fragile looking creature that dazzled Hollywood and took America by storm in the 50s was once quoted as saying, "For me, the only things of interest are those linked to the heart." She loved starring in comedies and they nearly always involved those matters of the heart she cared about so. Hepburn brought a childlike demureness to her roles, but her acting was tinged with class in a strange and fresh way unlike most of the other actresses of her day. She was typically modest about her abilities and possessed a remarkable integrity, which allowed her not only to retire at the apex of her career and devote herself to her family, but to continue to endear audiences in small roles all the way up to 1989 when she starred alongside Richard Dreyfuss in Steven Spielberg's Always.

Not only was Roman Holiday Hepburn's first foray into the Hollywood motion picture world (her acting up to this point was in French and British works), it was her first lead role as well-- and it was given to her with no prior lead experience.   Hepburn eventually went on to win an Oscar that year for her turn as Princess Ann, a young woman of foreign royalty that seeks a couple days of freedom as a normal girl-- a normal person-- when on a visit to Rome. Once again, as with A Room with a View, the majesty of Italy enraptures our heroine and she partakes in a slice of life she would never have tasted in the strict societal confines she and Lucy Honeychurch could likely relate to each other on, albeit on different levels.

Enter Joe Bradley, played by the restrained and marvelous Gregory Peck. Peck might not have been as immersed in romance as Hepburn, more famous for his various roles as troubled father (To Kill a Mockingbird, The Omen, Cape Fear) or sea captain (Guns of Navarone, Captain Horatio Hornblower R.N., Moby Dick, On the Beach), but he did try his hand in a few roles involving relationships with a female co-star including the aforementioned On the Beach and, perhaps most notably, Alfred Hitchcock's Spellbound. Peck once claimed that during this period, every romantic comedy script he read felt as if it were written with Cary Grant in mind. The trend understandably frustrated Peck, but nevertheless, when Roman Holiday came along, the man behind the smooth and full-toned voice and sly features hopped on board willingly enough to play the part of Joe Bradley.

Bradley is an American journalist assigned to a press conference the princess is scheduled to hold. He decides to skip out on the function and instead comes across the princess, calling herself Anya Smith, lying on a bench in the city. At first he believes Ms. Smith to just be a girl who has had a little too much wine during a night on the town (she's in fact merely fighting off sleep), and he grudgingly allows her to sleep on a particularly uncomfortable looking piece of furniture in his apartment. The following morning comes and a visit to his office reveals that the young girl asleep in his lodgings looks far too much like Princess Ann's photographs to be a coincidence. Bradley races back to his apartment in the hopes of getting a scoop on the stray blueblood and is surprised when she requests of him a day showing her around the city.

Taken at face value, Joe and Ann's adventures in Rome alongside Joe's photographer sidekick (an unexpectedly fantastic supporting performance by future "Green Acres" star, Eddie Albert) do not constitute a typical idea of a romance because, though they share some touchingly intimate moments, the two are never interested in becoming "romantically involved." Joe knows who Ann is and goes from chasing a story to happily accompanying her on an adventure. And Ann knows who she is and knows no relationship could ever exist between her and any man on her wild and whirlwind tour through the city; she has every intention of returning to her life, but she sees this as one last chance to breathe in the world as a girl before she becomes an adult and accepts her responsibility. The romance is there in full bloom, nevertheless. There is a passionate enthusiasm with each other and with drinking in the small joys of life together that no matter how momentary or ephemeral their time together is, it forms a lasting memory that allows Joe to re-evaluate his indifference towards everything and allows Ann to feel like a human being again, and in turn, re-instill a little love into the cold and sometimes detached position she holds in society. 

Roman Holiday is by far the most innocuous and lighthearted romp of the romance films we've discussed thus far. Even the mostly cheerful Pillow Talk and Down with Love had their moments of darkness that are wont to pop up in any genuine tale of love. It also has the least to say, but the gentleness of its story, the whimsical nature of its characters, and the performances by a fabulous Peck and the Princess of Romance herself, Hepburn, combine to form an unassuming film whose grace is tantamount to that of Hepburn herself.

21) Punch-Drunk Love (2002)

Continue on to Part Two of this edition of Observations Behind the Popcorn Bucket where I detail the next five entries in that which has become one hellishly arduous but incredibly fun (it's fascinating and amazing the complex web of relations and links you can find in these films) project.

NOTE: This week, as of this article's publication, two of the respectable members of filmmaking society I mention in this very segment departed this world.  Ismail Merchant of Merchant-Ivory Productions passed away at age 68 and Eddie Albert, most beloved for playing Oliver Douglas on "Green Acres", left us at age 99.
 
From this writer's point of view, they will be missed, but celebrated and I hope I have not become some DOOMBRINGER capable of felling celebrities with the very text I write.  Stay safe, Ewan!