When contemplating where a novelist should turn after one too many flops, “working as an escort” probably isn’t even remotely close to the first guess. As it happens, George Hickenlooper’s first film of the 2000s, The Man from Elysian Fields, deals with this exact scenario: Writer Byron Tiller (Andy Garcia), desperate to provide for his wife (Julianna Margulies) and family, turns to the unthinkable in an attempt to recoup his losses from several failed works. His first client, a woman by the name of Andrea Alcott (Olivia Williams), proves to be somewhat of a blessing in disguise to Byron when it’s revealed that her husband is none other than the famous Tobias Alcott (James Coburn), an alt-Hemingway who once won the Pulitzer but now struggles to finish the book he’s been working on for more than a decade.

It’s an absurd setup, to be sure, but it paves the way for a truly perplexing moral tale: Not only does Tobias approve of the relationship-for-pay between Byron and Andrea, but he actually seeks Byron’s help in restoring his long-gestating work to the level of gravitas that’s expected of an Alcott novel. Here, Hickenlooper presents the viewer with two separate ways for Byron to sell out: in his marriage and in his writing. It’s the kind of old-fashioned comedy of manners that props up the dated virtues that one would expect to find in the Golden Age of Hollywood. (If not for the Hays Code, of course, which surely would’ve taken issue with the whole male-gigolo thing.)

For the most part, Hickenlooper stands back and allows first-time screenwriter and longtime TV veteran Phillip Jayson Lasker to be the showoff. He cuts back on any distracting bells and whistles, likely out of fear of toppling the delicate balance Lasker’s script necessitates. Byron is truly in a bind, and his story is a tightrope walk that teeters between witty and pity. When things get increasingly irrational and veer toward unbelievable territory, Hickenlooper focuses on eliciting the solid, grounded performances demanded by something so preposterous (no easy task considering the genuinely outlandish places The Man from Elysian Fields ventures). Its comedy is more clever than gut-busting (inspired turn by Mick Jagger aside), creating a nice bookend of his 21st-century work opposite Hickenlooper’s only other overt comedy, Casino Jack.

Hickenlooper followed The Man from Elysian Fields with his last feature-length documentary, Mayor of the Sunset Strip. It’s one of the best underseen music documentaries. This might have something to do with the fact that it’s not actually about a musician: It’s about a man who gave musicians their big break. Not as an agent, a manager, or a songwriter, but as a chaotic hybrid of rock fanatic, music journalist, club owner, and radio DJ. His name is Rodney Bingenheimer, and, despite his crushingly lonely later years, he is owed countless debts of gratitude from the biggest names in music, stretching from the 1970s all the way through to the 2000s. Joan Jett. Coldplay. Gwen Stefani. David Bowie. Cher. Green Day. All got airplay on Los Angeles’ KROQ, all became superstars in the States, and all thanks to Bingenheimer.

That’s all fine and good — a true accomplishment, without a doubt, and one that would inspire pride in anyone — but Bingenheimer’s status as an iconic tastemaker of the California music scene and pillar of contemporary rock history is not the sole focus of Hickenlooper’s fascinating doc. Beyond the excellent soundtrack, the talking-head interviews, and the retelling of KROQ’s secret history, Mayor of the Sunset Strip doubles as a harrowing rumination on the notion of “celebrity.”

Similar to the almost fairy-tale-esque conundrum posed in The Man from Elysian Fields, Hickenlooper’s Mayor of the Sunset Strip details a mythical monkey’s-paw dilemma: What if you could send a whole slew of acts skyrocketing to the top of the charts but would fade into desolate obscurity yourself? For all that he’s done for some of the most instantly recognizable talents in the world, one would think that Bingenheimer was rolling in cash, set for life simply for playing those rock godheads he delighted in unearthing. Instead, the DJ — aka Rodney on the ROQ, the name Angelenos knew him by — lives modestly in a small apartment, the walls lined with photos of the celebrities he curated and catered straight to American listeners.

After following Bingenheimer around for six years shooting this documentary, Hickenlooper seems to have the starmaker’s dichotomies down pat: He’s both fame-obsessed and completely unknown. He’s rubbed shoulders with the greats, yet no one’s rubbing shoulders with him. He once was broadcast into millions of homes, but he lives alone. Perhaps Hickenlooper felt a strange sort of kinship with the man, having observed the making of multiple classic contemporary American films himself and directing several films deserving of a widespread acclaim that never arrived. Regardless of whether it was intentional or not, one can detect in Mayor of the Sunset Strip hints of Hickenlooper grappling with his own career as well as Bingenheimer’s. These feel especially poignant given the director’s too-brief career.

If The Man from Elysian Fields is Hickenlooper’s parable and Mayor of the Sunset Strip is his legend, then Factory Girl is his tragedy — not just because of its story but also because of the troubles it faced behind the scenes. Following the whirlwind rise and fall of Edie Sedgwick (Sienna Miller), an underground-film star and small-time celebrity who clicked with the likes of Andy Warhol, Bob Dylan, and Lou Reed, Factory Girl drew both the ire of those who knew the real Sedgwick and the frustration of the film’s producers. Namely Harvey Weinstein, who interfered with Hickenlooper’s vision, supervised reshoots, and monitored the editing process throughout post-production. In spite of its problematic nature, though, the film is worth examining as an emblem for Hickenlooper’s own experiences.

Think of it this way: Like Byron Tiller in The Man from Elysian Fields and Rodney Bingenheimer in Mayor of the Sunset Strip, Edie Sedgwick gets to brush up against some of the most important people of her era without ever truly having the opportunity to make it to their level. For Tiller, it’s Tobias Alcott. For Bingenheimer, it’s the rock ’n’rollers he plays (and parties) with. For Sedgwick, it’s that artistic, bohemian social group that was drawn to Andy Warhol’s New York studio in the 1960s. For Hickenlooper, it was Francis Ford Coppola, Peter Bogdanovich, Dennis Hopper, and the New Hollywood filmmakers that achieved the auteur status he was never quite granted himself.

Looking at it through this lens, Factory Girl plays less like a failed attempt at straightforward Oscar bait and more like one movement in an ongoing contemplation of celebrity status and the alienation that comes with it. For all its shortcomings — some no doubt caused by Weinstein’s intrusions — Hickenlooper’s penultimate film has value as a bleak look at the life of the famous-adjacent and the agony of being so close to (yet so far from) the big leagues. Although they couldn’t have been more different on the surface, Sedgwick and Hickenlooper’s similar untimely fates and their lifelong benching on the sidelines of fame sadly make them kindred spirits.

Just as Factory Girl eventually became mired in controversy because of its affiliation with Harvey Weinstein, George Hickenlooper’s final film, Casino Jack, would one day be tainted by its association to disgraced actor Kevin Spacey. Beyond this, though, there’s also the looming cloud of Hickenlooper’s tragic overdose. Claiming his life right before the movie was set to release, the filmmaker’s accidental death at the age of 47 is impossible to ignore when watching, discussing, or even thinking about Casino Jack. In retrospect, the film is a fitting if too soon conclusion to an underrated career that spans four prolific decades (from the tail end of the 1980s to the onset of the 2010s).

Based on a true story (like many of Hickenlooper’s other works), Casino Jack tracks Washington, D.C., lobbyist Jack Abramoff (Spacey) and the enormous corruption scandal that rocked the White House in the mid-2000s. His crimes of fraud, conspiracy, and tax evasion led to a six-year sentence for him — and plenty of additional charges for his network of lobbyists, congressional staffers, and White House officials. In addition to casting a particularly smarmy Spacey as his lead, Hickenlooper has stacked his supporting cast with a plethora of character actors like Barry Pepper, Jon Lovitz, Graham Greene, Maury Chaykin, and other vaguely familiar faces in bit roles that add further levity to an already-ridiculous story of real-life political debauchery.

Although Hickenlooper was obviously never a corrupt lobbyist on Capitol Hill, zooming out a bit reveals why the filmmaker would be attracted to Abramoff’s story: All the same elements that drew him to the tales of Tiller, Bingenheimer, and Sedgwick are present here. In every case, the central figures — flawed, lonesome, and true to life — thrive on being surrounded by the biggest stars of their industries. Their almost primal need to be validated by the ones at the top is inevitably what drives them to their lowest lows, their mentors and idols continuing to thrive while they’re left in the dust as if they never even existed in the first place.

There’s no telling what the 2010s and beyond could have held for George Hickenlooper. From his early days shooting Super8 student films with his fellow St. Louis University High Splicers to his untimely death on the eve of Casino Jack’s debut, Hickenlooper was thoroughly immersed in film for more than 30 years. As a creative and an outsider himself, it’s obvious that the director was drawn to people who fell under that same description — no matter if they were a struggling novelist, a trendsetting DJ, an underground socialite, or a sleazy lobbyist. He might not have reached the heights of Coppola or Bogdanovich, but he wasn’t necessarily trying to. He wanted to tell fascinating stories about people who interested him. As a result, he lived a fascinating life that should interest moviegoers everywhere.