Since we were kids, we knew the taxman was a bad guy. If we didn’t get the message from the lyrics of The Beatles, or the wolfish version of the Sheriff of Nottingham in Disney’s Robin Hood, then we learned through the very real anguish our parents suffered every year, mid-April. As we grew up, we likely heard comedians joke about the IRS, and every character but Jesus appeared to be unforgiving of any person who’d take a job in tax collection. Occasionally we’d see iconic IRS agents, such as the one Charles Lane plays in Capra’s film of You Can’t Take it With You, but even when memorable and enjoyable, they are still mostly identifiably villains. In Abbas Kiarostami’s first film, The Report (Gozaresh), the “hero” is a tax collector, yet he’s involved in corruption and beats his wife. Still hardly classifiable as a good guy, it would seem.
However, with all the movies made around the world in all the years of cinema’s existence, there had to be some films with likable taxmen, so we dug deep and desperately and just barely found ten such characters (admittedly, some are a stretch). While you struggle last minute with your 1040 today, you might not have much appreciation for a list of good guy taxmen, but we don’t care, because hopefully our celebration of these characters will keep us from getting audited anytime soon. Or, if we must get a visit from the IRS agent, we can hope we’re sent one like these men and woman:

“Bill Bradford” in Special Agent (1935)
Technically, Bradford (George Brent) is a newspaper reporter who only goes undercover as a taxman, but he’s at least been deputized by the IRS, so his work is official treasury business. His mission: find evidence against a gangster in order to put him away for tax evasion. Fortunately, he gains the help of the gangster’s secretary (Bette Davis), with whom he obviously falls in love. Made only a few years after Al Capone was similarly convicted of tax evasion, audiences must have been able to accept the IRS as heroic in such a premise.

“Tex Malinson” in Arizona Days (1937)
Singing cowboy Tex Ritter stars in this silly musical western, in which he takes a job as tax collector in Tombstone, Arizona, because the villainous Harry Price hasn’t paid his dues to the government. Yes, it’s a ridiculous idea, even though the film was made only a few years after the Capone case. Maybe in the bureaucracy of the 1930s tax evasion was the best way to bring down criminals, but in the Old West? When the bad guys kill your girlfriend’s kid brother, Tex, it’s time to let your guns do the convicting.

“Lorenzo Charlton” in The Mating Game (1959)
In this George Marshall-directed comedy, the bad guy is neither the IRS agent (Tony Randall) nor the tax-evading farmer he’s investigating (Paul Douglas). Initially, the stereotypically straight-laced Charlton represents a threat to the very likable Larkin family, but he does claim his job is to be of assistance to tax payers, and ultimately he joins their side against the true villain, a greedy and malicious neighbor. If there’s one thing to learn from The Mating Game, it’s that when faced with an audit, it’s best to have a daughter, preferably one as beautiful as Debbie Reynolds, with whom the taxman can fall in love. Interestingly, in a hopefully intentional nod to You Can’t Take It With You, Charles Lane shows up here again as another inspector from the IRS.

“Ning Cai Chen” in A Chinese Ghost Story (1987) and A Chinese Ghost Story II (1990)
Another bumbling tax collector (Leslie Cheung) with a good heart who falls in love while traveling for work. This film is quite different from The Mating Game, though, the main reason being that the love interest is a ghost (Joey Wang) who saves the taxman from being eaten by her master, a tree demon. Yeah, it’s that kind of Hong Kong martial arts fantasy, and it begat a couple sequels, including a remake and an animated film, as well as a TV series.

“Ryoko Itakura” in A Taxing Woman (1987) and A Taxing Woman’s Return (1988)
Director Juzo Itami’s follow-up to his hit comedy Tampopo, this satirical Japanese film is about a female tax investigator (Nobuko Miyamoto) whose latest job is to audit the owner of a chain of love hotels (Tsutomu Yamazaki). Apparently inspired by the filmmaker’s entry into a high tax bracket following the success of his first film (The Funeral), the position of tax agent isn’t exactly portrayed favorably, and certainly most of the film’s domestic audience wouldn’t be easily aligned with such a character, but there is definitely some likable qualities to Itakura, enough that she returned to the big screen a year later in a sequel that featured villains much worse than either tax collectors or tax evaders.

“Elliot Ness” in The Untouchables (1987)
While not technically a taxman, Ness (Kevin Costner) was an agent from the U.S. Treasury Department, and though he attempted to bring Al Capone down on bootlegging and murder charges, he ultimately had to settle on a conviction for tax evasion. So, he and his “Untouchables” were sort of a team of tax investigators, including the most taxman-like member, accountant Oscar Wallace (Charles Martin Smith).

“William Savage” in The Deceivers (1988)
In many Indian films, particularly those set in Colonial times, the taxman is as evil as the landowner. But in this Merchant Ivory film, a co-production from India and the UK, directed by Nicholas Meyer, a pre-Bond Pierce Brosnan plays a British officer, specifically a tax collector (or, as he prefers, colonial administrator) for the Honourable East India Company, who heroically investigates and then infiltrates the infamous Thuggee cult (which also showed up in Indiana Jones and the Temple of Doom) in order to destroy it from within.

“Harold Crick” in Stranger Than Fiction (2006)
The premise of this Charlie Kaufman wannabe involves a love story akin to that of The Mating Game and a fantasy plot even more unbelievable than that of A Chinese Ghost Story. And, as noted in a past list, another actress should have played the female lead instead of the intolerable Maggie Gyllenhaal. Still, Stranger Than Fiction gives us hope that at least a few IRS agents out there are as hilarious as Will Ferrell. We’d also be okay with Arrested Development’s Tony Hale, who plays Crick’s friend from work.

“Jack Goldwater” in Lady Magdalene’s (2008)
Goldwater (Ethan Keogh) may be the ultimate good guy tax collector, as the premise of this low-budget indie seems to combine the plots of some of the films examined on this list thus far. Like A Taxing Woman, it involves an investigation into a sex-based business (here a brothel), and like both A Taxing Woman’s Return and The Deceivers, the protagonist goes after a huge religious organization (here Al Qaeda). The movie’s main attraction is Star Trek’s Nichelle Nichols, who stars as the titular madam and performs a number of songs for the soundtrack, but for those of us who aren’t Trekkies and just can’t get enough heroic IRS agents, Lady Magdalene’s has additional appeal.

“Ben Thomas” in Seven Pounds (2008)
Because there are likely people who haven’t seen this film, who do still intend to see this film, and would prefer not to have any secrets spoiled, we will not discuss whether the protagonist (played by Will Smith) is a good guy or not, nor whether he necessarily fits on this list or not. We’re not recommending you watch the thing to find out what we mean, but if you’re curious and probably won’t ever rent it, check out the plot synopsis over on Wikipedia. One warning though: it’s a very confusing read.
I’m sorry to see that Bruce Greenwood in Exotica didn’t make this cut. Sure, he wasn’t recovering well from the murder of his daughter and subsequent death of his wife and that made him pretty grumpy. But he had depth for a Canadian taxman who spent too much time at the stripbar having his former babysitter dance for him.
I was kinda hoping that you weren’t going to have Will Ferrell in this, but there he was staring back at me when I came to this page from IMDb. His character was a douchebag, only saved by Emma Thompson’s meddling. But I could have lived with that, had it not been for the glaring omission of Rick Moranis in Ghostbusters.
Dr Ray Stantz: Are you okay?
Louis: Who are you guys?
Dr Ray Stantz: We’re the Ghostbusters.
Louis: Who does your taxes?
Dr Ray Stantz: You know, Mr. Tully, you are a most fortunate individual.
Louis: I know!
Dr Ray Stantz: You have been a participant in the biggest interdimensional cross rip since the Tunguska blast of 1909!
Louis: Felt great.
Dr. Egon Spengler: We’d like to get a sample of your brain tissue.
Louis: Okay.
Stranger Than Fiction is by far the best film on this list, and Maggie did an excellent job. Too bad this is the only thing Will Ferrell was ever any good in.
What about the Bon the Company Stooge (Bill) from Life Aquatic? They even rescue him from pirates
Neither Bill (Life Aquatic) nor Louis from Ghostbusters were taxmen. They were accountants who filed other people’s taxes.
And there’s no way in hell a movie can make me ever like a taxman.
I think an honorable mention should go to James Prufrock from the short-lived TV series “Push, Nevada”. That was one very determined individual.
What about Leo Bloom from “The Producers?” Or was he only an accountant?