Know Your Climates (Barack Obama) Phil Boerner met Barry Obama in the fall of 1979 when the two were freshmen at Occidental College, but they didn’t live together until after they’d both transferred to Columbia University two years later—by then they were already good friends. That said, Boerner, now the public-relations manager for the California Veterinary Medical Association, tells The Daily Beast there is one question he’d like revised on the roommate questionnaire: “One of the questions concerned whether you liked the dorm room hot or cold; that is, with the windows open or not on a mild evening. Well, it turns out that a student from, say, Hawaii, has a different standard of what's cold than a student from, say, New York, where there's snow in winter. So, it would have been nice if the administration had asked students to specify if they were using East Coast or West Coast standard.”

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Take Chances (Madonna)

It was Madonna who "loosened me up in so many ways and got me to take some risks," says Whitley Hill, the Material Girl's former college roommate from the University of Michigan. According to Hill, who kept detailed journals during that time, Madonna took her to a nude swimming hole outside Ann Arbor that could only be reached by descending a severely steep concrete embankment. "She just took off walking down that thing," says Hill. "She was just courageous like that, she was very driven and very direct." Direct enough to tell Hill about her mother's death from cancer the very first time they met. "I normally have something appropriate to say for just about any occasion," writes Hill about that moment in an unpublished memoir that she shared with The Daily Beast, "but I sure don’t have anything at this particular moment." Hill says Madonna even took her to her first gay bar in 1977. The two women were both members of the school’s prestigious dance department, and even then Madonna was a showstopper, says Hill. “Madonna's got her thigh between my legs and it's not just occupying negative space, it's really cramming in there," she writes of Madonna's dance moves. As for what they listened to? "Stevie Wonder," says Hill, "and Earth, Wind, and Fire was the primo dance record."

Watch Your Bedtimes (John Kerry)

"He was much the same as he is now," says Senator John Kerry's former roommate, Daniel Barbiero, who now works in financial services in New York. According to Barbiero, the onetime presidential hopeful was always "driven, politically active, competitive and with so much energy that he tired out anyone with him"—not necessarily the attributes you want in a roommate early on a Saturday morning. "We were three roommates with a two-bedroom suite and it was hands down that no one wanted to share [Kerry's] room," says Barbiero, "he was up a 5 a.m. and out late every day." Even back then, he says Kerry was an overachiever. "He was intensely interested in government and when JFK was assassinated, [Kerry] knew the name and job of every Cabinet member and leading legislator that we saw on TV during the funeral ceremonies."

Believe In Him (Owen Wilson and Wes Anderson)

Long before they made Rushmore and The Royal Tenenbaums together, screenwriting partners Owen Wilson and Wes Anderson were roommates at the University of Texas. Artistically, the actor and director clicked and remain close friends. But that was only after they learned to trust one another. "When I met Wes, he had just finished his first year at Texas and he told me he was going to be transferring to Yale soon,” Wilson once told the Los Angeles Daily News. “And I remember thinking, `What kind of fantasy world are you living in?' Because I knew he was a terrible student. But he said it with such conviction, I almost wanted to believe him."

Don’t Rush to Judgment (Michelle Obama)

“I was horrified.” That was Alice Brown's initial reaction when she found out her daughter, Catherine Donnelly, would be sharing a Princeton dorm room with a black student from Chicago, the future Michelle Obama. Brown told the Atlanta Journal-Constitution last year that she raced to the campus housing office and demanded a change. "I told them we weren't used to living with black people—Catherine is from the South," Brown said. Luckily, her daughter was not so quick to judge. “From the minute we met, I liked her,” says Donnelly, an Atlanta attorney. Two decades later, both mother and daughter found they liked Michelle’s husband for president as well. "We thought this is so ironic," Brown said. "[Michelle Obama] could be the first lady, and here we wanted to get my child out of her influence."

Be Patient (Warren Buffett)

In their first few days as roommates at Penn, Chuck Peterson found himself constantly hounding 17-year-old Warren Buffett to clean up after himself. “You left soap all over the sink, the towels on the floor, and it’s sloppier than hell,” Peterson says he told the young Buffett, according to Buffett biographer Alice Schroeder. Yet, when Warren Buffett started Buffett Associates in 1956, Peterson signed up as one of his first investors. “I learned real fast how bright he is and how honest he is and how capable,” Peterson told Schroeder.

Keep Them Grounded (Tiger Woods)

Fellow pro golfer Notah Begay III would never see the same glory on the PGA Tour, but Begay had a thing or two to teach Tiger Woods when the pair bunked together at Stanford in the mid-1990s. “My only goal with our relationship was to treat him as a normal person, and that's all I've ever done,” Begay told Golf Digest in 2000. “That meant studying together, showing him the way around the campus, introducing him in social situations.” Plus, Begay added, “You also made him carry the luggage on road trips.”

Opposites Can Attract (Robin Williams and Christopher Reeve)

“Right off the bat, we were a nice Frick and Frack. He was the class, I was the crass,” actor Robin Williams told Oprah Winfrey of his Juilliard roommate Christopher Reeve. The pair became fast friends, and when Reeve was paralyzed after a horseback-riding accident, Williams was one of his first visitors. “I came to him after he'd just come out the coma, because I came in as a Russian proctologist, and, ‘I just want to check the tube,” Williams remembered. “And he looked over and said, 'Hey, brother.’” When Reeve’s wife Dana died in 2006, Williams pledged to care for the couple’s son, Will.

Engage in Healthy Competition (Malcolm Gladwell)

Author Malcolm Gladwell may have been doing some field research for his book Outliers as far back as college when he roomed at the University of Toronto’s Trinity College with Jim Balsillie, the billionaire CEO of Research In Motion, maker of the BlackBerry. The pair hit it off betting on backgammon, posting the results of their matches prominently. "We played 15 games a day," Balsillie has said. "The great thing about backgammon is that if you win, you're a killer, but if you lose, you're just unlucky."

Give Him a Nickname (Ving Rhames)

When he entered SUNY-Purchase in 1979, Irving Rhames was a fledgling actor. Three decades later, he can command a million-dollar paycheck and has starred in dozens of films, including the Mission: Impossible series. Perhaps Rhames owes a small pieces of the credit for his fame to his freshman roommate and fellow thespian Stanley Tucci, who had the good sense to shorten Irving's given name to the catchier "Ving."

Be a Shoulder to Lean On (Soon-Yi Previn)

When Soon-Yi Previn's mother found out about her new beau, it was Soon-Yi’s Drew University roommate who comforted the college freshman after the angry phone calls. “I put my arm around her and said that if she wanted to talk about anything, I was there," Stephanie Dixon told Newsday in 1992. Of course, Previn’s mother was Mia Farrow, and the affair mother and daughter were arguing about was between Previn and Farrow’s longtime lover, Woody Allen, then 56. Previn and Allen have now been married nearly 12 years.

Find Common Interests (Adam Sandler)

“We all know what it’s like to be a little bit of a loser,” Jack Giarraputo has said of his work with fellow NYU dorm-mates Adam Sandler and Tim Herlihy. The threesome have collaborated on several hit comedies, including Big Daddy and The Waterboy. It was Sandler who convinced Herlihy to quit his Wall Street job to become a writer on Saturday Night Live, and in turn, Herlihy lent his name to one of Sandler’s most popular SNL characters, “The Herlihy Boy.”

Get to Know Their Folks (Eliot Spitzer)

Going to the Spitzers' house for dinner gave magazine publisher Bill Taylor an early glimpse into the family values of a man who would one day be a newsmaker. Eliot Spitzer, the disgraced former New York governor, was Taylor's Princeton roommate, and Taylor told Spitzer biographer Brooke Masters, “I used to study harder for a Saturday night dinner at the Spitzers' than I ever did for an exam at Princeton."

Don’t Take Things Too Seriously (Will Ferrell)

Maybe he was just practicing for Old School. “He played sand volleyball naked in front of 500 people... and then climbed up the side of the fraternity house,” Will Ferrell’s frat brother Craig Pollard told the New York Daily News. “Another time, our friend had to make an oral presentation in front of a big class and his professor. Will borrowed a janitor's uniform and mask and rubber gloves and went in and kept walking across the stage yelling, 'I was told somebody threw up in here. Where is it?'" But Pollard knew he could count on his old buddy when it mattered. Ferrell has lent his name to Pollard’s company, Will Ferrell Sunscreens, which donates 100 percent of its profits to a scholarship for young cancer survivors.

Stay in Touch (Geena Davis)

"We kid each other that had we known we'd both be presidents, we would have bought a piece of property somewhere," Nina Tassler has said of her Boston University roommate, actress Geena Davis. Tassler became president of CBS Entertainment, while Davis starred as the first female president on ABC’s TV drama, Commander in Chief.

Kathleen Kingsbury covers education for The Daily Beast. She also contributes to Time magazine, where she has covered business, health and education since 2005.

Jaimie Etkin is a culture intern at the Daily Beast.