Very rarely does the best coverage of a major event come from an unknown writer publishing on MySpace. But this year the most entertaining coverage of the Academy Awards and the A-list parties that followed came from none other than Laura Simpson, aka Jennifer Lawrence’s best friend and Oscar date. Simpson is likely best known to the public—or rather her back is—as the stabilizing force Lawrence grabbed on to for dear life after her highly publicized trip and fall (a sequel to her trip on the way to the stage last year). The fact that Simpson was only at the ceremony because of her friendship with Lawrence, and the fact that while everyone seemed to care that Lawrence fell but no one noticed Simpson almost did, perfectly captures the extreme highs and lows of being a celebrity best friend.

Celebrities are notorious for their entourages, so much so that the concept inspired a long-running show, Entourage, featuring the fictional Vinny Chase and the friends who knew him long before he made it big. According to Lola Ogunnaike, an anchor for Arise TV who previously served as an entertainment reporter for CNN, that’s the primary reason so many stars like keeping longtime friends close by. “Celebs like to surround themselves with their friends because it keeps them grounded and they believe those friends will be honest with them in a way their friends in the industry won’t be,” she says.

By taking a non-famous friend along for the ride, the celebrity benefits by having someone in the inner circle she knows likes her for being who she is, not for being rich and famous. And as Simpson’s Oscar adventure affirms, there are plenty of benefits for the BFF.

The most obvious is “getting to attend some of the most glamorous events in the world, thanks to your A-list friend,” says Alicia Quarles, correspondent for E! News. And not just attend them, but attend them for free. “Chances are, the film studio or whatever company the celeb is a spokesperson for is paying for the private or first class flights, five star hotels and top-notch dinners.” Ogunnaike wryly observes, “If Jennifer Lawrence is flying first class no one’s sticking her best friend in coach.”

Ogunnaike adds that besides the great events and great trips, there’s also another amazing perk of being a celeb friend: the never-ending free gifts—and not necessarily from the celeb. “The friends often get their hand me downs,” she says. But not the kind of hand me downs most of us are used to. “Celebs are given an endless amount of swag. Too much to actually use or wear so often they give what they don’t want to friends.”

“Unless they are hoarders, [celebs] don't keep most of it,” Quarles says. As a result “as their bestie, you get first dibs: couture clothes, shoes, bags, beauty treatments and vacations.”

In a nutshell, both entertainment experts summarized the benefits of being a celebrity best friend this way: you get the benefits of living like a celebrity without all of the hassle that comes with actually being one. But they acknowledged there are downsides.

“The VIP pal often becomes the VIP's coat holder as the star poses for pics [and] walks and talks on the red carpet,” Quarles explains. “Somebody has to hold their coat, and that is either the star's publicist, or their date.” Becoming the invisible coat-holder, or as Simpson explained in her essay, the one photographers scream at to get out of the “f*cking shot” perfectly symbolizes perhaps the biggest downside of being a celebrity best friend.

“If you are the best friend of a celebrity you are committing to a life living in their shadow,” says Ogunnaike. She noted that this is the way many celebrities prefer it. “A number of celebs want to be the only star in the relationship and make it a point to diminish anyone else.” There are some notable exceptions. For instance, Oprah Winfrey always championed her best friend Gayle King. While always a successful journalist in her own right, King expanded her national recognition in large part due to her many appearances on her best friend’s wildly popular talk show. Today King is co-anchor of The Early Show on CBS.

Other best friends of celebrities have managed successful transitions into the celebrity life as well. Kim Kardashian gained her first taste of fame as part of fellow celebutante Paris Hilton’s red carpet posse, while Cacee Cobb began her time in Hollywood as longtime best friend Jessica Simpson’s personal assistant. Cobb ultimately met and married Scrubs star Donald Faison, and now finds herself walking red carpets as his Mrs.

But perhaps the biggest downside of being a celebrity’s best friend: how abruptly it can all come to an end. “Celebrities can be very mercurial,” Ogunnaike says. “There are many people excommunicated from the entourage for no discernible reason except a celeb wakes up one morning and decides they no longer like you. It happens time and time again.” When it does happen, “There goes your friendship and your life of living in the lap of luxury.”