Jason Lee and 4 Other Celebrities Who Failed So Hard That They Probably Sleep On the Street Now and Use a Rat for a Pillow

Let’s face it: celebrities have it good. Our favorite movie stars and singers lead pampered existences full of decadence and carefree excess, gourmet meals, sex with supermodels in penthouses, swimming pools, mansions, yachts, polo, country clubs and of course the finest cocaine South America has to offer. 

But the greatest and most lasting perk of being a famous movie star or pop icon has to be the millions of dollars everyone on television, in movies or on the radio has, and will continue to have until they die, rich and beloved, worshipped by society as gods and buried in exquisite golden tombs. 

Yet somehow through a combination of bad luck, poor choices and low moral character, some celebrities tumble precipitously down the socioeconomic ladder and end up homeless trash, hobos sleeping on the street with a rat for a pillow. 

A formerly super-famous celebrity reduced to living on the street.

These sad failures were once the envy of their peers. Now they beg strangers for a moldy crust of bread to sustain them through the cold winter night. 

Granted, for legal reasons, we must concede that we don’t actually know that any of these entertainers are actually homeless, or even struggling financially, for that matter. But it’s been a while since they’ve had big professional successes so it seems safe to assume that they are all homeless now. We’re similarly going to assume that many of these has beens now wrestle with mental illness and/or substance abuse problems as well.

Pity these lost souls but do not hate them because no matter how foul their body odor or pathetic their lot, in some ways they are still human.

5. Jason Lee

The actor in happier times

Jason Lee segued smoothly from the world of professional skateboarding to movie stardom as a staple of Kevin Smith bro classics like Mallrats, Chasing Amy and Dogma. Lee made a mint as the cornpone star of the hit redneck sitcom My Name is Earl and lucratively hollered “Alvin!” as the human foil in the Alvin & The Chipmunks trilogy. 

Lee has had a cameo or a voice role here or there but he hasn’t otherwise done much for the past five years. So we’re going to assume that he’s traded in the red carpet for rummaging through dumpsters and fleeing paparazzi for running from railroad cops after stealing a sandwich from a dining car after days of not eating. 

Not too long ago Lee was looking for the next big, juicy role. Now he’s looking for a shelter that will let him stay the night despite his notorious night terrors and reputation for getting into drunken fistfights with staff. 

4. Freddie Prinze Jr.

Prinze Jr. with some former friends who now apparently won’t even let him crash on their couch until he gets his life back in order.

The son of legendary comedian and Chico and the Man star Freddie Prinze, handsome, likable Freddie Prinze Jr. was a central figure in the teen movie boom of the 1990s thanks to his starring turn as a jock who romances an outcast in the 1999 surprise smash She’s All That and hit 1997 slasher movie I Know What You Did Last Summer. 

The animated young actor played ascot enthusiast Fred Jones in Scooby-Doo and its 2004 sequel Scooby-Doo 2 Monsters Unleashed and even had his own eponymous sitcom, Freddie, in 2006. The show only lasted one season, however, and high profile roles have been few and far between since.

True, Prinze Jr. has wracked up some voiceover work in the past few years but that kind of sporadic employment can get a hard luck case like Prinze Jr. a 6 inch Subway sandwich and maybe a night or two in a fleabag motel, nothing permanent. 

Like all ambitious thespians, Prinze Jr. undoubtedly dreamed of winning an Oscar for his acting. Too bad he’s been reduced to living in a trash can like Oscar the Grouch. Prinze Jr. may not have a place to live or regular employment but at least he’ll always have his memories of playing ambitious baseball player Ryan Dunne in the 2001 romantic comedy Summer Catch. 

3. Phoebe Cates

Cates with a little creature she probably wouldn’t mind using for a pillow if no sewer rat was available.

Phoebe Cates made pop-culture history with the notorious bikini scene from the 1982 cult classic Fast at Ridgemont High, then played girl next door Kate Beringer in the hit 1984 critter comedy Gremlins and its wildly satirical 1990 sequel. 

Though not a hit with critics or audiences at the time of its release, the outrageous 1991 dark fantasy comedy Drop Dead Fred went on to develop a major cult following. 

Unfortunately Cates hasn’t appeared in a movie since 2001’s The Anniversary Party, which almost assuredly means that she’s joined the ranks of America’s homeless. Passerby once gawked at Cates because she was a beautiful, glamorous movie star. Now they look at her pushing a grocery cart containing all of her worldly belongings down a ghetto side street and see a grim cautionary warning of the ephemeral nature of fame and destiny’s unfathomable cruelty. 

The “gremlins” Cates deals with these days as a modern-day hobo are likely to include depression, drug abuse or even suicidal tendencies, which are all common among the transient population that now calls Cates one of its own. 

2. Jonathan Silverman

Silverman with a buddy as dead as his career.

Jonathan Silverman charmed his way into America’s hearts playing a Neil Simon surrogate in the coming-of-age play Brighton Beach Memoirs on Broadway and in the 1986 feature film. The affable young actor followed it up with 1987’s Caddyshack II, the high-profile sequel to Harold Ramis’ 1980 cult classic but the film bombed with critics and audiences alike.  

Silverman had more success, at the box-office at least, with the infamous dark comedy Weekend at Bernie’s, where he and Andrew McCarthy play scheming yuppies who must pretend that their dead boss is still alive for legal and financial reasons. The outrageous comedy was so successful it inspired a less successful sequel. 

The lanky comic actor had his own sitcom in the mid-1990s in The Single Guy but things have slowed down to the point where we’re now almost certain that Silverman, like many of his peers, has undoubtedly traded in a mansion and fabulous wealth for living in a cardboard box and spending his days scavenging for food and/or cheap hooch.

Silverman’s career as a movie star is deader than Bernie, the curiously expressive corpse who upstaged him during his brief prime as a leading man, but unlike Bernie in Weekend at Bernie’s 2, a voodoo priestess is probably not going to be able to resurrect his professional mojo via some manner of spell. 

Silverman may have been the Single Guy but these days he can’t score a single decent role that would lift him out of homelessness and finally give him back his dignity and self-respect. The Caddyshack II star would happily live in a shack at this point, or a hovel, but it’s achingly apparent that Silverman is doomed to die on the streets, just another casualty of the fame game. 

1. Brobee

Brobee’s not smiling much these days, alas.

Affable monster Brobee’s upbeat personality and guileless innocence and enthusiasm made him a fan favorite on the beloved kiddie hipster favorite television show Yo Gabba Gabba! The show was a big hit with kids and parents during its auspicious 2006 to 2015 run. Unfortunately the “little green one” hasn’t worked in years and consequently spends his days haunting soup kitchens in search of a warm meal and warding off the DTs by drinking fortified wine in various alleyways and public parks. 

Brobee no longer lives in Gabba Land. These days you’re more likely to find him on L.A’s skid row, his fur matted, his eyes bloodshot, staggering around in a Thorazine daze. Where he once sang happily of having a “party in my tummy” these days he’s more concerned with withdrawal symptoms if he doesn’t get some “methadone in my bloodstream.”

Sadly, Brobee has gone from hanging out with DJ Lance Rock to smoking crack rock. 

You might think that this is a particularly stupid, meaningless entry because Brobee is a fictional character from a children’s program that is no longer on the air, and therefore homelessness isn’t really an issue for him, or any of the other people on this list, for that matter. 

But the point of this list is not to have a point. Instead, it’s to randomly, ignorantly and anonymously shame celebrities for not being quite as famous or successful as they once were from the comfortable, judgmental distance of a freelancer’s laptop. In that light Brobee belongs on this list as much, and as little, as real human beings do. 

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