5. Drop Dead Gorgeous
Despite bombing with audiences and critics on its initial theatrical run in 1999, Drop Dead Gorgeous earned strong word of mouth due to its persistence within the home video market, and now thanks to its availability on streaming, it is a certified cult comedy classic. The film is blacky cynical and often abrasive with its offensive humor, as it details the fraught behind the scenes turmoil that occurs at a high school beauty pageant in the small town of Mount Rose, Minnesota. The satire of rural life, beauty standards, and televised pageants leaves almost no one unscathed.
The film draws together an incredible ensemble of actresses that would go on to break big, including Kirsten Dunst, Amy Adams, Denise Richards, and Brittany Murphy as various contestants who each have their own motivations for winning the contest. Additionally, the film features a wild selection of character actresses, including Kirstie Alley, Alison Janney, and Ellen Barkin as some of Mount Rose’s longtime residents who are accustomed to the strange traditions. The pseudo-documentary style of filmmaking helps to nail the biting wit of the script and the comedic bravery of the performances.
4. Adventureland
Great coming of age stories come every once in a while, and Adventureland is a fantastic look at the conflict and comradery that exist between coworkers at a small town job. Jesse Eisenberg stars as James Brennan, an ambitious college graduate who aims to visit Europe and attend graduate school at Columbia University. James feels like he’s prepared to launch his life and career, but thanks to unexpected financial issues, he’s forced to get a part-time job at a local amusement park and gain real world experience.
The humor comes from seeing James become adjusted to the working class lifestyle he’s never experienced. The staff is brought to life by a terrific ensemble; James falls for Emily (Kirsten Dunst), a girl with a troubled home life who has fallen for James’s superior Mike (Ryan Reynolds), a struggling musician. Bill Hader and Kristen Wiig also give scene stealing performances as a quirky couple that manage the park. Perceptive of both the aspirational yearnings and hard hitting realities that young people face, Adventureland is a truly special film with a fantastic soundtrack.
3. The Commitments
There are many comedies that focus on creating a band, but few are able to capture the reality that most bands break up, and even fewer make it big. The life of a musician is hard and often thankless, and The Commitments finds the joy in the moment, as a quirky ensemble of makeshift performers travel from gig to gig. Jimmy Rabbitte (Robert Arkins) is an ambitious young manager who scours the working class to craft the perfect soul band.
Jimmy’s journey is filled with struggle; he’s barely able to keep his combative group of performers together, no one shows up for rehearsal, and each venue presents a new challenge. However, when it gets down to it, the band puts on a great show, and it’s easy to understand why Jimmy cares so much about getting his music out there. Now regarded as one of the best Irish movies ever made, The Commitments should continue to make waves as a classic that intertwines working class struggles and an amazing soundtrack.
2. Kicking and Screaming
Noah Baumbach’s directorial debut isn’t just a brilliant deconstruction of the cynicism and ego of higher level education, but one of the most entertaining hangout movies ever made. Baumbach’s astonishing first feature follows a group of college students who all wrestle with their graduation; despite claiming to be world weary and done with the cycle of classes, they’re woefully unprepared for the real world, and Baumbach finds the charm in turning this cynical group into more sincere people.
Characters like Grover (Josh Hamilton), Chet (Eric Stoltz), Otis (Carols Jacott), and Max (Chris Eigman) have years of history together, and Baumbach does a great job at showing how the years of self-congratulation have isolated these characters in an absorbed bubble. Seeing each of these characters confront their anxieties- such as Grover’s quest for “the one that got away”- leads to some hilariously awkward scenarios. Baumbach would go on to become one of the generation’s most acclaimed directors with films like The Squid and the Whale, Frances Ha, The Meyerowitz Stories, and Marriage Story, but it’s worth checking out where he started from.
1. Igby Goes Down
A perfect embodiment of white collar self-absorption and 21st century coming of age anxieties, Igby Goes Down is a relentlessly clever dark comedy that deserves to be heralded as a classic. The film is quick to satirize the wealth gap and goes to great lengths to show the level of privilege granted to those who care more about self-image than anything, but it’s also undeniably sympathetic to the plight of its lead character- he’s hopelessly out of touch with any semblance of reality, and despite his best efforts, he’s not able to fit in anywhere.
Jason Slocumb Jr. (Kieran Culkin), nicknamed “Igby” thanks to a cruel family joke, is 17-years-old and has managed to flunk out of every private school his domineering mother (Susan Sarandon) has signed him up for. Weary of his young Republican older brother Ollie (Ryan Phillippe), Igby breaks free from his family and enters the art scene in New York, all while avoiding his sly godfather D.H. Banes (Jeff Goldblum). The real world proves to be a difficult place for Igby; he doesn’t know anything about the reality of making a living or the perils of heartbreak, but he’s more terrified of falling into his family’s footsteps than anything.
Kieran Culkin gives an astonishingly good child performance; he nails the quippy, snide dialogue that Igby uses as both a deflection and means of coping with the complicated world around him. Igby’s means of destroying his mother’s plans and trying to craft his own image are often hilarious, but his growing realization that he’ll never recover from his youthful trauma is quite heartbreaking to watch. It’s an astonishing debut for filmmaker Burr Steers, who incorporates great artwork and an era accurate soundtrack to craft this unique story. Now that Culkin is getting the best reviews of his career for his performance on Succession, it is worth checking out this sorely underrated comedy favorite.