April 15th seems like an appropriate date to discuss taxing movies, right? No, not movies which are strenuous to watch (such a list could be endless), but films which feature a tax issue as a key part of its plot and/or has an Internal Revenue Service agent as a prominent character. Let me further refine the criteria to exclude popular historical tax references – Roman collections (like those at the time of Jesus’s birth), Robin Hood, the Boston Tea Party, Al Capone, etc. – to keep this list from getting too long. While most classic movie fans can readily recall at least one version of The Merry Widow, I found it difficult to remember more than a handful of films whose storylines related to this uniquely American “holiday”:

• The Last Gangster (1937) – O.K., first off (at least, chronologically), I had to cheat my own rules. Though the title character in this one isn’t Al Capone, Edward G. Robinson’s Joe Krozac does get put away for ten years in prison at Alcatraz for tax evasion in this crime drama.
• The Falcon in San Francisco (1945) – only a brief reference near the beginning of this eleventh film in the Falcon series; with his detective boss Tom Lawrence (Tom Conway) aka The Falcon, sidekick Goldie (Edward Brophy) discusses the possibility of reducing his own income taxes by getting married
• The Joe Louis Story (1953) – though this is a below average biographical drama about the titled champion prizefighter, it details the real fact that he had to reenter the ring after retiring in 1949 in order to pay off a $200,000 tax debt to the Internal Revenue Service.
• The Mating Game (1959) – Paul Douglas (in his last feature film role) plays a farmer that “horse trades” for everything he needs such that he has never had to pay any income taxes (he’s never even filed a return!). George Marshall directed this romantic comedy that features Tony Randall as a persnickety I.R.S. agent that’s sent to investigate this travesty after a disgruntled wealthy neighbor reports Douglas’s unauthorized activity. The situation gets complicated when Randall meets the farmer’s daughter, played rambunctiously by Debbie Reynolds (who was dealing with personal issues, like husband Eddie Fisher leaving her for Elizabeth Taylor, at the time).
• The Young Philadelphians (1959) – may mark the beginning of tax lawyering in film; within a few years, several others follow which features clients pursuing a course of action or scheme to dodge or avoid paying taxes per their attorneys’ suggestions. Paul Newman plays a lawyer who decides to specialize in this relatively new field within his firm; it enables him to win a client (Billie Burke) away from his ex-fiancee’s father (John Williams).
• Ada (1961) – while the tax reference in this drama doesn’t strictly fit the criteria outlined, it’s always nice to see a movie that tells it like it is in state and federal politics. Dean Martin plays a fairly clueless yet elect-able good ole boy that’s handpicked by an insider (Wilfrid Hyde-White) to be the front man empty suit that will rubber stamp his pork barrel legislation, which will require raising taxes on the constituency.
• Bachelor in Paradise (1961) – the notorious author of a series of “sex around the world” books that Bob Hope plays in this comedy returns to the United States after 14 years abroad to find that his accountant has absconded with his earnings and never filed any tax returns for him. So, his publisher (John McGiver) sets him up in the titled San Fernando Valley suburb incognito where he can do the research to write a “Sex in America” book, and pay his back taxes. Lana Turner plays his landlord; Janis Paige, Paula Prentiss, and Virginia Grey play his housewife neighbors.
• The V.I.P.s (1963) – the character that Orson Welles parodies in this Elizabeth Taylor-Richard Burton “trapped in an airport” drama provides some much needed comic relief; he plays a famous foreign movie producer-director that needs to get out of the country before midnight to save $1 million in taxes. Since all the flights out of London are delayed until the next day, his moneyman proposes another plan – Welles’s character must marry the foreign bimbo actress, with whom he is traveling, to (somehow) avoid paying the tax man. Of course, it’s just a coincidence that this movie is set in England, the country of George Harrison and the Beatles.
• The Wheeler Dealers (1963) – James Garner plays a Texas wildcatter that’s a master of tax law such that he can turn losing investments into winners, or at least limit his businesses’ losses, in this romantic comedy directed by Arthur Hiller that also features Lee Remick and at least a dozen recognizable character actors.
• Hot Millions (1968) – screenwriter Ira Wallach, who worked on less than a handful of films (all comedies), shared an Academy Award nomination for this comedy’s story and screenplay with its star Peter Ustinov. Wallach’s first screen credit was for Boys’ Night Out (1962), a movie featuring Garner and Randall with Kim Novak, his second was the Garner feature listed above, and this was his fourth and last. It also includes a tax reference: the white collar criminal that Ustinov plays does the warden’s taxes while in prison, a chore done to engender favoritism that was nefariously performed by Tim Robbins’s character in The Shawshank Redemption (1994).

What other classic movies can YOU think of which feature “taxes or I.R.S. issues”?