During the run of the very popular television sitcom Friends, the main cast members attempted to capitalize on their newfound clout in the industry by trying to jumpstart film careers with varying degrees of success. For every Scream (featuring Courteney Cox), there was a Fools Rush In (Matthew Perry) or Ed (Matt LeBlanc) or The Pallbearer (David Schwimmer). Like her castmates, Jennifer Aniston’s cinematic track record was rather uneven, but in 1996 she appeared in two independent films, including the little-seen yet charming romantic comedy Dream for an Insomniac along with Ione Skye. The film was written and directed by newcomer Tiffanie DeBartolo and, despite Aniston’s star power, was barely released, flopping spectacularly at the box office, which is a shame because it is a smart, engaging rom-com that flew in the face of a lot of Generation-X movies being made at the time.
Like its star, Dream for an Insomniac is breathtakingly gorgeous, from its sumptuous black and white cinematography to its inevitable transformation into color, which also sets it apart from films of its ilk. The opening scene plays homage to classic Hollywood cinema with its black and white look and Ione Skye dressed up like Audrey Hepburn in Breakfast at Tiffany’s (1961). “Novocaine for the Soul” by the Eels plays over the opening credits as we see Frankie (Ione Skye) – the insomniac of the film’s title – struggle to sleep (I’m not sleep deprived, I’m sleep deficient.”). If that weren’t enough, she’s unlucky in love, but it may be that her standards are too high with the personal credos like, “Anything less than extraordinary is a waste of my time.”
She lives above a café that she works at when not going on acting auditions with her best friend Allison (Jennifer Aniston) and in a week they plan to move to Los Angeles to pursue their career in earnest. Uncle Leo (Seymour Cassel) is an old school Italian man who owns the coffeehouse and worships Frank Sinatra, as does Frankie. He keeps hoping that his son Rob (Michael Landes) will find a nice girl and settle down, seemingly unaware that he’s in fact gay.
Dream for an Insomniac ambitiously maintains its dreamy black and white look for the first 20 minutes until Frankie meets David (Mackenzie Astin), the guy who just started working at the café, and notices his blue eyes. It is at this point that the film comes vividly to life as their meet-cute scene involves testing each other’s literary prowess as they have to figure out who the other is quoting, from Aristotle and Tennyson to Fast Times at Ridgemont High (1982) and Raising Arizona (1987).
Frankie is a hopeless romantic that believes in passionate love, a dreamer unable to sleep and who is not only drawn to David’s intelligence (and good looks), but the fact that he is also a struggling writer. Her admiration for him only deepens when she reads some of his stuff. Unfortunately, he suffers from writer’s block, much like she’s plagued by bouts of insomnia. He promises to help her sleep and she aims to conquer his inability to write.
I always wondered why Ione Skye’s career didn’t take off after Say Anything… (1989), but maybe she wasn’t interested in doing big studio films as evident in subsequent efforts like The Rachel Papers (1989) and Gas Food Lodging (1992), which were small films that tended to fly under the radar. She often plays characters that possess a keen mind and Dream from for an Insomniac is no different as Frankie is a lover of the written word. I’ve always felt that Skye is a classic beauty and she adopts a stylish retro look in this film that compliments her features, including that warm, inviting smile. I like how DeBartolo includes little bits of business, like Frankie’s daily ritual of getting up in the morning and tossing pennies at Rob’s window across the way until he surfaces and she greets him with a literary quote. It provides us with some insight into these characters and the relationship between them.
Jennifer Aniston has a small, but significant role as Frankie’s best friend. She playfully adopts a variety of accents throughout (including French, Irish and Canadian) much to the mild annoyance of her friend, but this isn’t overplayed and serves as a reminder that she’s a struggling actress much like Frankie. Aniston is a gracious performer in this film as she doesn’t try to steal a given scene even though she is the biggest star in the film. She supports Skye and the two play well off each other as they portray convincing best friends. Allison is there for Frankie, consoling her when she finds out that David has a girlfriend and they spend an afternoon commiserating over pizza. It also makes one wish that Skye would get more lead roles this one and that Aniston would do fewer studio movies and take on roles in smaller films that don’t require her to do all the heavy lifting.
In the ‘90s, Mackenzie Astin effortlessly bounced between studio films (The Evening Star) and indie movies (The Last Days of Disco). He’s good enough as Frankie’s potential love interest and intellectual equal. He seems to have decent chemistry with Skye, but lacks the charisma required for the role. Again, this typifies the film’s desire to go against the trend of other Gen-X films with their proliferation of trendy hipster poseurs, like ones Ethan Hawke plays in Reality Bites (1994) and Matt Dillon in Singles (1992).
Michael Landes (Lois and Clark: The New Adventures of Superman) plays a gay man refreshingly devoid of all the cliché affectations that you see in most Hollywood movies. Rob is a guy that just happens to be gay and his dilemma is working up the courage to come out to his father, which is dramatic enough. Rounding out the cast is Seymour Cassel, who, by that point, had become an elder statesman of indie cinema and his presence in this film gives it some credibility, almost making us overlook the quaint Italian stereotype that is his character.
The few critics that saw Dream for an Insomniac were not crazy about it at all. In his review for The New York Times, Stephen Holden called it a “self-conscious modern sitcom that with its San Francisco setting suggests a pale shadow of Armistead Maupin’s Tales from the City.” The Los Angeles Times’ Kevin Thomas wrote, “It’s likely to be no more than a blip on the screen for its appealing actors, who’ve done fine work before and since this wan effort was finished three years ago.” However, in her review for the San Francisco Chronicle, Barbara Schulgasser wrote, “All of the playful dialogue – and this movie is joyfully full of talk – is handled well in DeBartolo’s savvy script and given life by actors who seem to truly embody the idealism of the characters.”
The machinations of Hollywood soured director Tiffanie DeBartolo from making another movie: “It was a life I really didn’t want to lead. I value my privacy, and the solitude of writing. Making films necessitates a lot of schmoozing and game playing and socializing that I just didn’t have in me. That said, I really did love the experience of being on the set and watching my words and my vision come to life.” She went on to become an author, writing two novels – God-Shaped Hole and How to Kill a Rock Star – and co-founded indie record label Bright Antenna.
Dream for an Insomniac is the forgotten Gen-X film and it wouldn’t be a ‘90s rom-com without all the characters frequenting a coffeehouse, the inclusion of a trendy hipster poseur, a few choice alternative rock songs, and a discussion about popular culture in an amusing scene where Frankie and her friends argue over a game of Scrabble about the relevance of Bono and wondering if his status as reigning rock god has become eclipsed by the likes of Eddie Vedder and Michael Stipe. That being said, this film succeeds where a lot of its contemporaries failed by staying relevant after all this time. It now comes across as some kind of postmodern Gen-X fairy tale rather than a postmodern Gen-X reference guide, which films like Reality Bites and Empire Records (1995) resemble.
That’s not to say Dream for an Insomniac doesn’t reference pop culture that was en vogue at the time, but it largely quotes from literary references that include writers like Jim Morrison and Charles Bukowski from various time periods. Literature makes up more of the film’s DNA than the references to film and television. This makes the film something of an anomaly in the Gen-X subgenre. Dream for an Insomniac flies in the face of other Gen-X movies with its cultural touchstones, the look of its characters – they aren’t all wearing flannel – the use of Frank Sinatra music as opposed to whatever Seattle music was trendy at the time, and even the coffeehouse setting lacks the fashionable clutter of pop culture décor that you see in films like Reality Bites and Singles.
If Slacker (1991) and Reality Bites represent the polar opposites of Gen-X cinema with the former epitomizing lo-fi indies and the latter an example of mainstream studios, then Dream for an Insomniac hews closer to Slacker. It is a Gen-X rom-com thankfully devoid of the irony that plagued most of its contemporaries, which has helped it age well over time. It is an underrated gem anchored by an engaging performance by Ione Skye that deserves to be rediscovered.
Ders, Kim. “Tiffanie DeBartolo: Amazing Grace and Rock ‘n’ Roll.” MusePaper. July 18, 2008.