I didn’t even know we had made a Dane Cook documentary, and it gave me a Tourgasm. Boy, I wanted it to. Ultimately, though, despite my adoration of Dane Cook, and despite the fact that he seems to have fallen completely and totally out of fashion, I struggled with Funny Money: The Dane Cook Story. The documentary is interesting if you know nothing about the situation involving Dane and his half-brother, Darryl McCauley, who stole millions of dollars from him while managing his finances. Dane and Darryl apparently had a strong familial connection despite technically being half-brothers, which obviously makes what happened even more devastating. Eventually, the authorities get involved, and now, years later, we have a documentary about how spectacularly everything fell apart. Somehow, I actually missed most of this story when it originally happened, probably because it occurred around the same period when the culture had started paying considerably less attention to Dane Cook.

Cook had risen rapidly during the early 2000s, with his college audiences helping propel him into this strange stratosphere where he was packing enormous venues and selling comedy albums in ridiculous numbers. That’s when I first caught onto Dane Cook, through friends who had bought one of his comedy albums. From there, I watched the stand-up specials and his HBO series Tourgasm, which followed Cook and fellow comedians Gary Gulman, Jay Davis and Robert Kelly on the road. I’ve also seen plenty of his film work, including Employee of the Month, Good Luck Chuck, My Best Friend’s Girl, Dan in Real Life and Mr. Brooks. I was even hoping his NBC sitcom Next Caller would eventually surface somewhere after the network famously shelved it before airing a single episode. Perhaps someday it will casually materialize on Tubi or YouTube so we can all finally enjoy the series NBC decided we weren’t allowed to watch. Dane had a very specific brand of humor that rubbed some people the wrong way, so even at the height of his popularity, he attracted a passionate group of haters. I frequently found myself defending Dane Cook in much the same way Nickelback fans found themselves defending Nickelback. Somehow, being incredibly popular made them deeply uncool.

I mention all of this because I think it’s important to be open about my bias going into the film. Yes, I am a Dane Cook fan. I even casually mentioned after watching the last season of The Traitors that I would love to see him cast on the show. Based on everything I’ve seen of him over the years, I think throwing Dane in as a wild card could be fascinating. He has the kind of large personality that might actually survive that environment rather than retreat into the background. Funny Money only reinforces that impression. Cook comes across as someone who is as unafraid to speak his mind sitting in front of a documentary camera as he has traditionally been standing onstage.

Funny Money takes us briefly through Cook’s childhood, his complicated family structure, his decision to pursue comedy and eventually his move to Los Angeles. He began attracting a younger audience than many of the comedians working the clubs around him, and once college students discovered him, his career exploded. With that success came more money and the need for people he trusted to help manage everything. Darryl had been working as a corrections officer before suffering a serious injury after being attacked by an inmate. Dane saw an opportunity to help his brother by bringing him into the business. Darryl could handle bills and some of the day-to-day financial responsibilities while Dane could essentially overpay him as a way of supporting him and his wife, Erika. Unfortunately, putting family and enormous amounts of money together turned out to be a catastrophic combination. Darryl suddenly had access to an increasingly massive fortune, and eventually Dane discovered that the person he trusted with his finances had been stealing from him. From there, the investigation takes over, and I don’t think you need to know much more going in because discovering exactly how enormous this became is part of what makes the documentary interesting.

One thing I appreciated about Funny Money is that it at least attempts to investigate the situation from more than Dane’s perspective. Dane naturally speaks more than anyone else, but Erika becomes the documentary’s most important counterweight because Darryl himself does not participate. She is left discussing events Dane wasn’t present for while also speaking about her own involvement and, to some extent, Darryl’s. However, the documentary makes a very peculiar choice by prominently introducing the fact that Erika identifies as a witch. I found myself wondering why that information was relevant. We don’t explore her beliefs. We don’t learn what being a modern witch means to her. This isn’t suddenly Witchcraft in America: The Erika McCauley Story. It’s simply dropped into the documentary, and because it has virtually nothing to do with the financial story, I couldn’t help feeling like its inclusion was intended to make certain viewers immediately question her credibility.

That bothered me because the documentary doesn’t need to do that. Erika is perfectly capable of creating questions about her judgment through the things she actually says and admits to doing. Depending on how you interpret her account, she can come across as naive, complicit, willfully ignorant or some combination of the three. Those are relevant questions because they relate directly to the crime and her relationship with Darryl. Her religious or spiritual beliefs do not. If you substitute “witch” with almost any other niche belief system or identity and ask why a filmmaker would deliberately highlight it without meaningfully exploring it, the manipulation becomes fairly obvious. Let Erika’s own words determine whether the audience believes her. There is enough there already without putting an unnecessary thumb on the scale.

The larger problem is that Funny Money goes on far too long. I’m not someone who routinely complains about runtime because runtime itself is irrelevant. You can make a 75-minute movie that feels three hours long, and you can make a three-hour movie that flies by. Runtime is ultimately about pacing and whether every scene, interview and storytelling choice earns its place. Funny Money feels like a documentary that needed another aggressive trip through the editing room. There’s repetition, there are points that get driven home after they have already been firmly established, and the filmmaker occasionally interjects to provoke a response without becoming enough of an onscreen or offscreen presence for that technique to develop into anything meaningful. There’s a tighter, more compelling 90-minute documentary buried somewhere inside this nearly two-hour version.

There’s also something slightly misleading about calling this The Dane Cook Story because it really isn’t. If you know nothing about Cook, you’ll get the Cliff Notes version of why he became famous, but this is hardly a deep dive into his career. We don’t meaningfully examine the comedy itself or spend much time with his famous routines. Tourgasm barely factors into the story despite being an important piece of his rise. Next Caller isn’t explored, even though Cook shot multiple episodes of an NBC sitcom that the network canceled before broadcasting any of them. His controversies are largely sidestepped as well, including the accusations over the years that he stole jokes and the way that reputation became part of the public perception surrounding him. Even Cook confronting Louis C.K. about those accusations on Curb Your Enthusiasm would seem like a natural part of a documentary genuinely interested in examining the arc of Dane Cook’s career. Funny Money isn’t particularly interested in any of that because, despite the title, this isn’t really the Dane Cook story. It’s the Dane and Darryl story.

That leaves me strangely twisted on the film because, as someone who didn’t know all of the intricacies surrounding Darryl taking the money and running, I found that part genuinely interesting. It also provides some context for a period when Cook’s career was changing dramatically, although I wouldn’t necessarily draw a straight line between the theft and every professional choice he made afterward. Ultimately, Funny Money is less interested in understanding Dane Cook as a comedian, actor or human being than it is in allowing him to tell an extraordinary cautionary tale about what happens when someone you genuinely love and trust has access to virtually everything you’ve earned. Once you recognize that, the documentary makes more sense, but it also makes the subtitle feel designed to rope in Dane Cook fans expecting a much broader examination of his life and career.

The documentary also does not have audio description, which created another problem for me. Dane and Erika dominate so much of the film that they became relatively easy for me to track, but additional family members, friends and interview subjects come and go without the accessibility necessary for me to always know exactly who is speaking. Dane’s sister Courtney is among the more recognizable additional voices, but an audio description track identifying speakers and providing access to the documentary’s visual information would have made a significant difference. For a documentary so dependent upon interviews, archival material and the audience understanding who is providing each piece of information, accessibility shouldn’t feel optional.

Mostly, I came away disappointed, but not entirely dismissive. There is absolutely something worthwhile here for viewers who want to understand what happened between Dane Cook and Darryl McCauley and how their relationship completely collapsed. Maybe part of me is also simply rooting for Dane Cook to find his way back into something high-profile. I’d like to see what he does next. Funny Money is messy, overlong and strangely incomplete as a portrait of the celebrity whose name is in its title, but buried underneath all of that is an extraordinary betrayal and an unfortunately timeless lesson: pay attention to your own finances. Trust is wonderful, but nobody should have unchecked control over everything you’ve worked for simply because they happen to be family. We’ve heard versions of this cautionary tale before, and we’ll undoubtedly hear them again. Funny Money gets there by a very circuitous route, but it gets there. With a slim margin, I recommend Funny Money: The Dane Cook Story, while continuing to wait and see what comes next for Dane Cook.

Fresh: 6.4/10