‘Dear Eleanor’ is a Road Trip Movie to Nowhere

For eight seasons and a movie, Kevin Connolly was best known as E from Entourage, perhaps the pinnacle of the dude bro subgenre of macho inanity. Now that Entourage is thoroughly in the rear view window, Connolly is spreading his wings as a feature film director. His latest effort, Dear Eleanor, is a coming-of-age road trip movie featuring two teenage girls on a quest to travel across the United States and meet Eleanor Roosevelt in the summer of 1962. For the life of me I’ve been unable to figure out why one of the stars of the douchiest shows to ever grace the small screen would be the right director for a story of an adventure of two teenage girls, and the finished product of Dear Eleanor doesn’t provide many answers.

Set in 1962, Dear Eleanor is the story of Ellie Potter (Liana Liberato), a teenage girl in Central California who recently lost her mother in tragic accident. Her father Bob (Luke Wilson) isn’t handling the tragedy in the best manner, sometimes shirking his parental duties to pass the time in a local bar, leaving Ellie with the burden of responsibilities. Ellie’s mother was a great admirer of former First Lady Eleanor Roosevelt and died while on her way to give a speech introducing her hero. Knowing this, Ellie’s best friend Max the Wax (Isabelle Fuhrman) sends a letter to the former First Lady expressing Ellie’s admiration. The letter is answered not by Mrs. Roosevelt but by Billy (Joel Courtney), a young man with a crush on Max, who writes kindly words under the guise of the former First Lady. This inspires Ellie and Max to sneak off and hit the road towards Mrs. Roosevelt home in upstate New York.

Leaving their California homes just before the start of the Cuban Missile Crisis, it would seem that Ellie and Max are about to take a road trip through a certain period of American history, a period of fear and uncertainty. Except the film quickly drops the aspects of the Cuban Missile Crisis and all aspects of history aside from a few casual references to old movies and the death of Marilyn Monroe. Instead these two characters take a road trip through the Road Trip Movie Guide Book, including a stopover where they find a hunky rancher (played by Patrick Schwarzenegger), pick up a fugitive from justice (played by Josh Lucas), and pick up Max’s cousin, a showgirl with heart of gold (played by Jessica Alba). Meanwhile, they must elude the authorities as Ellie’s father and Bobby have teamed up to find the runaway teenagers.

Connolly and cinematographer Steven Fierberg give the film an aesthetic of Technicolor pastels that one might find in a generic ‘50s diner. That’s really emblematic of the film’s adherence to a candy colored look at this period in American history. Ellie and Max traverse across the nation but never encounter a segregated South or towns in the throes of nuclear panic. They simply encounter a clichéd scenarios like eating in a diner with their fugitive buddy when two cops enter – something we’ve seen countless times before. The script from Cecilia Contreras and Amy Garcia is just a collection of missed opportunities for some introspective look at the American heart in favor of saccharine sentimentality for an America that never truly existed.

The pacing of Dear Eleanor is one of the more bewildering aspects of this underwhelming road trip. Nearly an hour into this trek across the nation and our characters have only gotten as far as New Mexico, with a rote little montage to speed the characters across the continent in a couple of minutes.

Dear Eleanor is like a bad road trip, countless stops along the way to see things that you’ve already seen before or of just little interest. When it matters most, the film takes a shortcut through what could’ve been its most fascinating aspects in favor of the most rote storytelling imaginable. Kevin Connolly doesn’t show much flair as a director, but neither does the script that he’s working with. Dear Eleanor is a disappointing movie because there’s a nugget of good idea in its concept, one that’s never even found in the slightest on the screen. Once it’s all over, you realize that is was one long road trip to nowhere.