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Welcome to Obscurity: 15 of Hollywood's Greatest Underrated Films Worth Watching

Updated on December 19, 2019
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Heather has a Bachelor's Degree in English from Moravian College and has been freelance writing for more than 14 years.

The Rocky Horror Picture Show movie poster
The Rocky Horror Picture Show movie poster
The Sure Thing movie poster
The Sure Thing movie poster
Carlito's Way movie poster
Carlito's Way movie poster
Fearless movie poster
Fearless movie poster
The Sweetest Thing movie poster
The Sweetest Thing movie poster
P.S. movie poster
P.S. movie poster
Kiss Kiss Bang Bang movie poster
Kiss Kiss Bang Bang movie poster
Going the Distance movie poster
Going the Distance movie poster
The Upside of Anger Poster
The Upside of Anger Poster
O Poster
O Poster
Boiler Room Poster
Boiler Room Poster
In Her Shoes Poster
In Her Shoes Poster
Keith Poster
Keith Poster

In less than two weeks, the Oscars will be determining once again what 2010 films deserve to be recognized for their excellence. It's too early to tell whether the awards will be given to the right winners or the wrong ones. The nominated films have been widely profiled in the press, theatres and other award shows. It's safe to say that films such as Black Swan and The King's Speech are the cream of the crop. What makes those films stand out while others get ignored for various reasons? Misleading previews? Bad timing? Tricky subject material?

Here are a list of 15 films that have for one reason or another not been given their proper due. Those films are divided into five categories ranging from mobster flicks to the hard to define films that weren't properly marketed. Read through the list to see where your favorite films may rank and discover new ones to see over the weekend.

Overshadowed By Their Predecessors

Talk Radio (1988)- Picturea cross between 1987's Wall Street and the vulgarity of 1992's Glengarry Glen Ross to fully understand this film. Eric Borgosian played a controversial radio show host who enjoyed pushing buttons during his show and in his life. On the eve of national syndication, he finally started to realize the error of his ways, but he was too late to rectify anything. Borgosian had a chance to reconcile with his ex-wife but spurns her to protect her from his life's growing complications. It was obvious that he would be done in by his success one way or another. The way his demise truly came about was brutal, unexpected and something to talk about. Unfortunately, Radio came out after Wall Street that wasn't fully appreciated until David Mamet perfected his sharp tuned dialogue in his films in the 90's.

Carlito's Way (1993)- When Director Brian De Palma and Al Pacino teamed up in 1983's Scarface no one expected the cinematic magic would be repeated by them. Scarface was a shocking look of a gangster's rise and fall from power. Fast forward to 1993's Carlito's Way with another De Palma/Pacino film as a recently released from jail gangster who tried to live a crime free life. Unfortunately, his former associates won't allow him that luxury and the battle for supremacy ended with the ultimate sacrifice. Unlike his intense Scarface character, Pacino portrayed Carlito Brigante as a wisen criminal with years of experience behind him. He tried not to always resort to extreme violence, or acting. That opportunity was given to costar Sean Penn as Pacino's drug addicted lawyer. Carlito's Way didn't have the same impact as Scarface because the film lacked the shock factor as Scarface. It had a quieter impact that most audiences overlooked and should be given a second glance once again.

Casino (1995)- Sadly, Casino was doomed to be ignored from the start because moviegoers were destined to compare it to 1990s far superior Goodfellas. Sure, De Niro and Pesci did their best to rectify that by portraying two friends running the odds in a mobster heavy Las Vegas. Both men rose through the ranks and were eventually done in by it. Of course, their mutual destruction came in the form of the deceptive Sharon Stone. She seduced both men and bled them dry, until she became collateral damage as well. Check it out at your own risk, and try not to think it's Goodfellas because it's anything but.

Bawdy Comedies

The Sure Thing (1985)- When it came to 80s comedies, John Cusack reigned supreme in films ranging from Say Anything to Better Off Dead. It was in this film that allowed Cusack to truly shine as a college student looking to score a guaranteed night of passion without romance. He was so desperate for it that he had to travel across country to get it, but he didn't expect to fall in love with fellow traveler Daphne Zuniga instead. Thing introduced Nicolette Sheridan to the masses and was sorely overlooked for its shallow subject matter when it should be included in future John Cusack marathons.

The Sweetest Thing (2002)- A sharp comedy that tried to take cues from There's Something About Mary minus the hair gel gag. Cameron Diaz, Selma Blair and Christina Applegate played three friends looking for Mr. Right Now. They decided to put love on hold until something better truly came along. Diaz received the ultimate surprise when she believed she found Mr. Right and would do anything to find him, which resulted in crashing his wedding to someone else. The Sweetest Thing didn't get its proper dues due to a less than stellar R Rated cut of the film, which was rectified with the hilarious Unrated cut on DVD. Rent it tonight to enjoy some of the film's hysterical undiscovered moments.

Going the Distance (2010)- Distance was dismissed due to its end of summer release date last year. The movie featured real life couple Drew Barrymore and Justin Long as a bi-coastal couple trying to make it work and failing miserably. They were forced to eventually choose between their relationship and their respective careers. It was still sweet to watch, even through the ending was obvious from the beginning. The toilet humor might've been misplaced at times, but that can easily be overlooked.

Dramas with a Message

Fearless (1993)- Jeff Bridges portrayed a man who survived a devastating plane crash and completely abandoned his fear. He was able to eat Strawberries, which he was allergic too. His character threw himself into every dangerous situation imaginable. The only thing that could save him was his family to bring him back to reality. Fearless was one of Bridges' most underrated films because he delivered a riveting performance that allowed him to flirt with adventure and his sanity. The serious subject matter was considered a turn-off to the audience and should be a topic of discussion. At least for the ambigious ending alone.

Boiler Room (2000)- The best way to describe Room as a b-grade Wall Street. A young stockbroker wants it all but none of the consequences. He realized that his success wasn't truly his and his life was in danger. Room was also one of the few films that allowed Vin Diesel a hand at acting before he threw himself into too many action films. See this movie instead of the multiple Fast & Furious sequels.

P.S. (2004)- Is it a love story or a second chance story? Laura Linney played a College Admissions employee who gave up on ever finding true love. She was surprised when a potential student came into her life that proved her wrong. P.S. was an indie that never reached a proper audience until Netflix came along.

Hard to Label Films

The Rocky Horror Picture Show (1975)- The ultimate underappreciated film that is usually dismissed in its first viewing. Show offered some strange characters(a transvestite scientist and aliens) and songs worth singing along with. The movie might've offered some cringeworthy moments, but it still needs to be watched at least twice in a lifetime. At least to avoid the dreadful follow-up film.

The Upside of Anger (2005)- A comeback role for Kevin Costner as a washed up baseball player finding love with a bitter mother of three (Joan Allen) as she dealt with her husband leaving her. The two grew closer together as her daughters grew up before her eyes. The chaos reached its peak when the family realized what happened to the missing patriarch. What happened after that was almost like the aftermath of an enjoyable hurricane. Anger's movie family was one that everyone would want to be a part of during the holidays only.

Kiss Kiss Bang Bang (2005)- Is it a comedy? A noir? A drama? Who cares! It was hysterical to watch Robert Downey Jr. portray a man who preferred to be a fake somebody than himself. He submerged himself headlong into a dangerous situation that only PI Val Kilmer can get him out of, unless they kill each other first.


Adaptations

Romeo Must Die (2000)- Die is best described as an urbanized Romeo & Juliet with some kung fu thrown in for good measure. It's considered to be one of Jet Li's best American films to date partly because of his chemistry with the late Aaliyah. The film should also be remembered for the Aaliyah song "Try Again" that signified the relationship between the main characters. A good date movie for guys and girls.

O (2001)- An update Shakespeare adaptation set in a private school full of social upheaval. A stormy relationship between a basketball player and his girlfriend (Julia Stiles) wrecked by a jealous friend that ended in death. O was deemed controversial due to the nature of the school shootings that plagued the U.S. at the time. It's release was delayed so many times that audiences waited to see it on DVD instead.

In Her Shoes (2005)- Based on the bestselling novel about two sisters who had nothing in common, except their shoe size. Party girl Maggie (Cameron Diaz) often took advantage of her dependable sister Rose (Toni Collette). It takes a shocking betrayal and a reunion with their maternal grandmother (Shirley MacLaine) to repair their relationship. Shoes didn't get its proper respect because audiences had a hard time seeing Diaz as anything but a romantic comedy girl. She made a valiant effort that should eventually get her a different kind of notice. The film's biggest revelation was MacLaine underplaying her usual flashy performances to deliver her most memorable one to date.


In the end, it's hard to say why certain films don't get the recognition they deserve, but you have the opportunity to view them now with the innovation of Netflix and OnDemand. Decide for yourselves what obscure film deserved to be added to your favorites list. Sometimes by chance in the form of a teen drama (Lost and Delirious or Keith), a sequel (International Velvet) or a technology innovation (Tron). Take a chance on the next movie you watch. It could surprise you.

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