Hollywood is a tough place to succeed. It is saturated with aspiring artists that are desperate to achieve fame and fortune. When you are a struggling actor or musician working towards fame, the reality of living on a paltry (or non-existent) salary can threaten your dreams of stardom. It is common practice for Hollywood hopefuls to live with roommates, to reduce the burden of their expenses, while they are trying to jumpstart their careers. Even better, it provides them with a place to lay their head where they can commune with other artists enduring a similar struggle. This type of emotional support can make the difference between miserably pining away at a seemingly intangible fantasy and happily toiling toward the achievement of professional goals.
Though the odds of making it are low, and the chances of roommates achieving success in Hollywood even more rare, there have been instances in which this has happened. Whether the stars were perfectly aligned in the favor of both roommates, or they were both extraordinarily talented, this phenomenon does occur from time to time. Most people are familiar with the longtime friendship between actors Ben Affleck and Matt Damon. The two moved in together while co-writing the Oscar-winning script for ‘Good Will Hunting’. Their friendship has endured the test of time, as Damon listed his Miami family home for sale and moved into a Pacific Palisades community a few miles from Affleck’s home in 2012. However, what other celebrities have had roommates that also went on to become famous?
The list of famous former roommates includes:
13 Ryan Gosling and Justin Timberlake
Timberlake’s mother assumed guardianship of Gosling for the duration, allowing him to continue filming while his mother returned to work in Canada. Each has gone on to celebrity stardom and Gosling told the press that though they are no longer close friends, they will always be supportive of one another.
12 Jamie Foxx and Rascal Flatts
11 Lindsey Lohan and Raven Symone
Former child stars, Lindsey Lohan and Raven Symone once rented an apartment together. Reportedly, Lohan kept her clothes in the apartment but never really moved in, only visiting the premises a total of 3 times. The ‘That’s So Raven’ star has been quoted as saying rooming with Lohan was a “cool experience” because she never saw her, but received rental payments for 14 months.
10 Robin Williams and Christopher Reeves
Comedian Robin Williams and actor Christopher Reeves were roommates at the Julliard School of Drama. The pair went on to build successful careers in Hollywood and become lifelong friends, until Reeves passed away in 2004. Before his passing, Williams had supported the ‘Superman’ star after his paralysis in 1995 and was active in The Christopher Reeves Paralysis Foundation. Williams even pledged to take care of Reeves' son after his mother died two years later.
9 Owen Wilson and Wes Anderson
Actor Owen Wilson had a fruitful experience with his college roommate, director Wes Anderson. The two were roommates while attending the University of Texas. Anderson went on to co-write the film script that led to Olsen’s acting debut, ‘Bottle Rocket’. The film was Anderson's directorial debut and also starred Owen’s brother, Luke Wilson. Since college, the Hollywood movie veterans have maintained their allegiance and Wilson has gone on to star in numerous films by Anderson.
8 Danny DeVito and Michael Douglas
In the 1960’s, Danny DeVito shared a New York City apartment with Michael Douglas. The actors went on to become household names and work together on various film projects, including ‘One Flew Over the Cuckoo's Nest,’ which DeVito appeared in and Douglas produced. Douglas reportedly refers to DeVito as “Danny D” and calls him his “oldest friend in the business”.
7 Robert Downey Jr. and Kiefer Sutherland
On Jimmy Kimmel Live! actor Robert Downey Jr. disclosed that he was once a roommate with Kiefer Sutherland. The ‘Ironman’ star claimed that he shared place in L.A. with Sutherland for 3 years. Downey reported that those were the years in which Sutherland was new to L.A. and was struggling to build his career in Hollywood. The two starred in a 1988 film ‘1969’ which also featured Winona Ryder.
6 Al Gore and Tommy Lee Jones
While upperclassmen, the two became close and even formed a country band together. The friendship between Gore and Jones has persisted and Jones even spoke at a Democratic National Convention on behalf of his former roommate.
5 Conan O’Brien and Jeff Garlin
Comedian’s Conan O’Brien and Jeff Garlin had an enterprising experience as roommates in Chicago while reaching for fame. The two launched a pet-care service to make ends meet. The ‘Curb Your Enthusiasm’ star still has his former roommate's back as he famously slammed late night host Jay Leno for taking O’Brien’s promised time slot, which led to O’Brien’s subsequent departure from ‘The Tonight Show’ in 2010.
4 Marilyn Monroe and Shelley Winters
Former Hollywood bombshells Marilyn Monroe and Shelly Winters once co-habitated. The actresses shared an apartment in the late 1940’s, while they were acting students in New York City.
The Oscar-winning actress told the press that she was a role model for Monroe who took her cues from Winters' fashion and career choices. Winters went on to write a tell-all book about her experiences in Hollywood, including her time spent living with Monroe.
3 Stanley Tucci and Ving Rhames
Actors Stanly Tucci and Ving Rhames bonded while rooming together as drama students at the State University of New York at Purchase. Tucci even reportedly gave Rhames the nickname ‘Ving’, an abbreviation of his first name, Irving. Even though Rhames transferred to Juilliard School's Drama Division, the two kept in contact and remain friends.
2 Jude Law and Ewan McGregor
Actors Jude Law and Ewan McGregor roomed together before they were famous along with Law's ex-wife (shown in picture) Sadie Frost. The two reportedly met at a 1990 audition and went on to co-found a production company together called Natural Nylon. McGregor supported his long-time pal after his break-up with Sienna Miller by accompanying him on a motorcycle excursion through South America. The pair also completed a photo shoot together (shown above) with legendary photographer Lorenzo Agius in 2009.
1 Penn Badgley and Milo Ventimiglia
‘Gossip Girl’ star Penn Badgley claims to have learned the ropes from former roommate actor Milo Ventimiglia. Penn moved in with Ventimiglia, who was 10 years his senior, when he was 18 years old and trying to make his mark in Hollywood. The ‘Heros’ star reportedly helped Penn get into clubs and taught him how to navigate the Hollywood scene.
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