Company | Brown & Williamson, 1979-1983
Brown & Williamson paid its product placement agency $278,000 in retainers from 1979 to 1983 to put its brands in nearly two dozen Hollywood movies.
In addition, over this period the product placement agency billed Brown & Williamson $687,500 to pay off individuals in at least ten film productions. 
$70,000 was reportedly paid to at least one film.  Sylvester Stallone struck a multi-picture product placement deal for $500,000; Brown & Williamson paid out at least $300,000 on this agreement (additional reference).
In 1983, Brown & Williamson reported to the Federal Trade Commission that it spent a total of $85,000 in the “testimonials and endorsements” category that the FTC then used to monitor product placement.
Note 1 | Brown & Williamson's 1983 internal audit of its product placement program summarizes retainer payments to Associated Film Promotions (AFP) and "special" payments purportedly delivered to producers, actors, prop masters, and others in the film industry.
In-kind payments, including cars worth $160,000 allegedly given to Sylvester Stallone, Clint Eastwood, and Paul Newman, are detailed in Brown & Williamson's audit worksheet. In a letter, Brown & Williamson terminated AFP’s product placement activities as of March 1984.
Note 2 | AFP proposed that $70,000 be paid to the movie Tempest, starring John Cassavetes and Gina Rowland; Brown & Williamson made the payment. Disappointed in the results, Brown & Williamson discussed “make-goods.”
Despite other problems uncovered in its 1983 product placement audit, Brown & Williamson's follow-up memorandum outlines how the program might be continued: “Where a star actually smokes our brands in a manner clearly visible to viewers and our presence in the movie is more apparent,” for example, the tobacco company considers payments of $100,000-$250,000 per movie.
With RJ Reynolds, Brown & Williamson merged into Reynolds American in 1994. British American Tobacco owns a 42 percent stake in that company, which acquired Lorillard in 2015.