The Tragic Real-Life Story Of Hollywood Boulevard Superman

The autumn of 2019 brought us terrible news: Superman was dead. Not the comic book character, mind you. He's probably doing as well as a man attacked by supervillains on an hourly basis ever can. Instead, we lost the actor who played — no, embodied – the role of Superman far longer than the likes of Christopher Reeve, Brandon Routh, Henry Cavill, and Tom Welling. As TMZ reports, we're talking about Christopher Dennis, the famous Hollywood Boulevard Superman, who unexpectedly passed away at 52 in the San Fernando Valley. 

Dennis was a long-tenured street performer and quite easily the best-known of the many colorful characters lining the stretch of Hollywood Boulevard between Madame Tussauds and Hollywood & Highland Center. During his 25 years portraying the role, he became a well-known and popular fixture in the area, and even soared to heights of fame well beyond his usual stomping grounds, thanks to his TV appearances and a documentary about his life. 

Unfortunately, Dennis' life wasn't all cloudless skies, flowing capes, and amiable photos with admiring tourists. On the contrary, his existence was filled with strange, sad, and bewildering events that ultimately culminated in his untimely passing. Many people knew about him, but few can say they truly knew what he was going through. It's time to take a behind-the-scenes look at the tragic real-life story of Hollywood Boulevard Superman.

Hollywood Boulevard Superman's mysterious early years

What kind of man just grabs a cape and tights one day and spends the next quarter-century pretending to be the greatest superhero of them all with an almost child-like passion? What kind of childhood did the man himself have? Was he permanently stuck in his kid years due to some past trauma, or seeking revenge because his parents were gunned down in an alley? And if it's the latter, how come he didn't dress up as Batman?

It's difficult to say, really. We don't have solid answers to any of those questions, as there's very little information about Christopher Dennis' childhood or, for that matter, his life before he became Hollywood Boulevard Superman. According to Movieweb, the situation wasn't exactly helped by Dennis himself, who appeared to prefer his past to be multiple choice. He has been known to claim that he's an orphan, which is a tragic yet perfectly legitimate past for an aspiring superhero. However, Dennis also insisted that he's an illegitimate love child of Sandy Dennis, the Academy Award-winning actress. Regardless of which story is true (if either), he certainly seemed to gravitate toward tragic childhood stories, so it's possible that whatever his actual formative years were like, they weren't all that happy.

Hollywood Boulevard Superman's painful origin story

As murky as Christopher Dennis' formative years may have been, we know quite well what prompted him to become the legendary Hollywood Boulevard Superman — after all, Dennis himself revealed his origin story in an interview with the Superman Homepage. He used to be an aspiring actor who found it difficult to juggle his auditions with his job as a waiter. But when people on set started telling him he looked like Christopher Reeve, he began thinking. One day, he was cast as a reporter with a very Clark Kent-like appearance, and as a joke, he put a Superman T-shirt underneath the suit. When someone inevitably asked whether he has a Superman suit underneath, he ripped open his shirt to a truly magnificent effect. 

Now confident that he could portray Superman entertainingly enough, Dennis ditched his waiter job and started constructing his Hollywood Boulevard Superman persona. Unfortunately, the transition turned out to be quite painful ... literally. He constructed the costume bit by bit, and got so carried away with his quest for authenticity that the only appropriate boots he could find were a way too small pair he found at "a ladies' exotic shoe place." Until the size 12 Dennis could upgrade to better footwear, he spent his days standing on the Boulevard smiling through the awful pain and bloodied toes these crushing boots were causing him.

Hollywood Boulevard Superman and fleeting fame

It's hard to get noticed in Hollywood, but the task gets considerably easier when you're a large man who spends the bulk of his days playing the world's most iconic superhero on the neighborhood's most famous street. As the Hollywood Boulevard Superman's reputation grew, so did his popularity, and before long, Christopher Dennis found his fame growing well beyond the reach of your average street performer. 

Hollywood Reporter tells us that he became a frequent, much-liked face on Jimmy Kimmel Live! and even ended up on the cover of The Hollywood Reporter with Kimmel. Dennis was also the main focus of Confessions of a Superhero, a documentary about him and three other street-side superheroes. His popularity also got him sporadic acting work, usually as either himself or some variation of his Hollywood Boulevard Superman character. 

As IGN notes, it's the documentary that reveals the tragedy lurking beneath the veneer of his fake muscles and all-American hero appearance. Despite Dennis' success and fame, Confessions of a Superhero shows parts of him that come across as a desperate and sad, borderline delusional man who's "nearly lost" in the Superman role. To be fair, more or less the same applied to the other three stars of the documentary.  

Hollywood Boulevard Superman's divorce and start of darkness

It's anyone's guess when exactly things started going south for Hollywood Boulevard Superman. However, the Los Angeles Times tells us that the Boulevard rumor mill has a few ideas. According to fellow performers, Christopher Dennis' decent into darkness probably coincided with the time his first marriage fell apart. It's unclear when the divorce happened, but Dennis was apparently pretty serious about the relationship: As the Superman-themed Super Museum tells us in their Facebook statement, he married the "love of his life" on their premises, under a massive Superman statue. In an interview for the Superman Homepage, Dennis has said that the museum was a familiar place for him and his wife, who he reveals was called Bonnie. According to him, they once spent $35,000 on merchandise there.   

The reasons behind their eventual divorce are unclear. One possible reason is that Bonnie may have tried to force Dennis out of his Superman lifestyle, and he ultimately chose it over her. While the whole "$35,000 on merchandise" thing would certainly make this story believable, there's another, much darker potential reason for their marriage falling apart. Hollywood Boulevard Superman might have already found his kryptonite: Crystal meth. 

Some say that Dennis eventually got married again, in a Las Vegas type affair that may or may not have actually taken place in Vegas. This marriage was allegedly rather brief, and to someone who was reportedly just making poor Superman's downward spiral worse.  

Hollywood Boulevard Superman ended up homeless

Entertaining as it may be, street performing is not the most stable of jobs, and even the most revered, friendly performers like Christopher Dennis might be secretly living in squalor and wrestling with all sorts of demons. One of Dennis' demons was homelessness. As the Guardian and the Los Angeles Times tell us, Hollywood Boulevard Superman used to live very near his Hollywood Boulevard haunt, in an apartment filled with Superman merchandise and DIY Man of Steel dioramas. Unfortunately, he lost the place at some point and ended up on the street, possibly after spending some time living in a mobile home. Dennis also said that he was beaten up and robbed during his homeless days, and described these desperate times as his "own living hell." 

What's worse, he's not the only Hollywood Boulevard "character worker" who has faced a similar situation. In fact, many costumed Hollywood Boulevard panhandlers reportedly say that their peculiar performing job is basically the only thing that keeps their motor running.

Hollywood Boulevard Superman's darkest hour

Hollywood Boulevard Superman was no stranger to struggles, but the misfortunes he suffered in the last few years of his life must have made that one of the most challenging periods. As the Los Angeles Times reports, Christopher Dennis was living in a motor home a few years before his death, but the city decided to take it away. Now without a place to stay, things only got worse for Dennis when a homeless man beat him up with golf clubs and robbed him of his costume, money, and laptop. CBS Los Angeles tells us Dennis took these events extremely hard. "I felt like I was dead because I was now without a job," he said. "I lost my dignity and my pride."  

It must be noted, however, that according to some of Dennis' associates he never even owned an RV, so the story of his wheeled shelter being seized should possibly be taken with a pinch of salt. And while Dennis did tell the story of his golf club assailant, the allegation that he might have been embellishing the motor home story doesn't necessarily make him the most credible source. 

Hollywood Boulevard Superman's kryptonite was crystal meth

Every version of Superman has his kryptonite and according to the Los Angeles TimesHollywood Boulevard Superman's was crystal meth. Christopher Dennis struggled with addiction for years, and despite many attempts he wasn't able to fully kick his habit. Combined with his homelessness and financial troubles, the crystal meth addiction left him in a very unhealthy state of mind. While most everyone who met him in his Superman guise found him charming and "unfailingly polite," Dennis was a wreck in his private life. He was struggling with depression and taking a number of medications, and he was even known to self-harm.

Eventually, Dennis stopped working the Boulevard, though he always wanted to return. His costumed colleagues say they still saw him around after he left the game, though they didn't always recognize him. At that point, the former Superman had become a shadow of his old self — a mumbling, skinny, disheveled wreck sketching stuff in his notebooks and looking "decades older than he was."

Hollywood Boulevard Superman may have scammed donors and helpers

A drug addiction can do terrible things to even the nicest of men. While few people have bad things to say about Christopher Dennis as a human being, the Los Angeles Times tells us that his crystal meth habit, poverty, and a Hollywood Boulevard denizen's propensity for tall tales may have somewhat stretched the Superman's trustworthiness towards the end of his life. There are those who say that his story about losing his RV and ending up homeless is patently untrue because he never even owned one. Some even think that the tragic tale of Dennis getting robbed and beaten up by a golf club wielding homeless man never happened, and Dennis actually lost the teeth the altercation allegedly cost him to crystal meth.  

With these question marks hovering over the Hollywood Boulevard Superman's stories, it's worth noting that each report of his misfortunes led to news coverage, which in turn led to crowdfunding campaigns that sent thousands of dollars his way. At the time of his death, donors were "repeatedly" trying to reach him because he hadn't made good on his promised pledge rewards. What's more, well-meaning people also kept buying him new Superman suits so he could at least regain his means of employment and get back on his feet. One after another, the costumes disappeared ... and if you ask the Boulevard crew, these incidents tended to coincide with Dennis mysteriously acquiring more meth. 

Hollywood Boulevard Superman's last lease in life

Toward the end of his life, at a point where his costume (as well as most of his hope) was gone, Hollywood Boulevard Superman found an unexpected bright spot in the form of Jennifer Masciopinto. According to the Los Angeles Times, Masciopinto met Christopher Dennis on the street while he was sketching, and the two got to talking. Masciopinto, who uses a wheelchair and has cerebral palsy, had a boyfriend at the time, but when he started getting violent, Dennis stepped in and convinced her to join him "to get cigarettes." From that point on, they were inseparable. Masciopinto says Dennis "protected and cared for her even when he didn't care enough for himself," and she returned the affection by staying with him whether they were living in a tent or at a sober living home. 

A year or so went by. According to Masciopinto, the two were making good progress and "right on the verge of recovery." There was even a housing voucher looming on the horizon, which would enable them to live happily together and maybe, just maybe, allow him to return to Hollywood Boulevard to pursue his Superman dreams. And then, all of a sudden, she found him dead.

Hollywood Boulevard Superman's death was even sadder than you think

Everything in the Hollywood Boulevard Superman's story could easily lead one to believe that he died of a drug overdose. However, as the Los Angeles Times reports, the truth is somehow even more tragic than that. On November 6, 2019, TMZ broke the news of Christopher Dennis' death, and that his body had been found "lying headfirst" in a clothing donation bin. Because everything in this story apparently needs to be as awful as possible, the person who discovered Dennis was his partner Jennifer Masciopinto, whose wheelchair he had borrowed to reach the clothes in the bin and who had to enlist outside aid to be able to walk to the scene.

Masciopinto eventually clarified the circumstances that led to Hollywood Boulevard Superman's untimely demise at 52. Dennis had built a rope tool to get clothes from the donation bin, and used to stand on her wheelchair to fish the garments out through the lever-operated slot. Masciopinto usually accompanied him, but this time he decided to go alone and leave her sleeping. What happened next is anyone's guess: "Maybe he slipped," Masciopinto says. "Maybe he suffocated." 

Regardless of the exact events of the final moments of Dennis' life, the tragic end result remained, and when she found him the next morning, the paramedics could only pronounce him dead. Hollywood Boulevard Superman passed away alone and trapped, trying to get his hands on some warm clothes. 

Hollywood Boulevard Superman's unfortunate legacy

While media outlets and social media reacted to Hollywood Boulevard Superman's passing in somber sadness, the Los Angeles Times reports that many of his Boulevard associates had no pity for Christopher Dennis, the man who used to be the biggest of them all. After all, Dennis was showered with more attention than anyone else in his costumed crew during his 25-year tenure on the Boulevard. He had been handed opportunity after opportunity, and every time he messed up, fans and friends jumped to rescue him. Yet, he kept throwing away each and every lifeline with his self-destructive behavior and penchant for "tall tales," digging his pit a little deeper and pushing himself away from redemption with each self-imposed, meth-fueled failure. Such is his legacy among his peers. 

As for Dennis himself, he was acutely aware of the dangers of his chosen lifestyle, even before drugs took control of him — after all, Confessions of a Superhero opens with him saying: "Hollywood is a place where dreams are made and dreams are broken." However, he appears to have believed that in the end, he could go against the grain and become one of the winners. The Hollywood Boulevard Superman was familiar with the alleged "Superman Curse" that had killed four Superman actors before him, and once stated in an interview for the Superman Homepage: "I'm the mold that's gonna break that curse." Unfortunately, he wasn't.