Entrepreneurs Walt and Annette Kowalski discovered aspiring painter Bob Ross in the early 1980s, offering to house and feed him if he taught painting classes they’d arrange. That led to an Indiana public TV affiliate launching Ross’s “The Joy of Painting” in 1983, soon syndicated to more than 200 other stations, and so Ross and the Kowalskis formed Bob Ross Inc. to manage the series and a spinoff line of art supplies. As Ross’s celebrity grew, he attempted some brand extensions on his own, which irked the Kowalskis, as did an unfavorable shift in Bob Ross Inc. ownership shares in 1992 after the death of Ross’s wife and stakeholder, Jane Ross.
As Ross’s death approached in 1995, Walt Kowalski pushed him to sign a contract that would grant rights over all his work in perpetuity in exchange for a 1% profit share for 10 years. Ross wouldn’t sign and then rewrote his will, excluding the Kowalskis and leaving control of his name, image, and work to his son Steve and half-brother Jimmie Cox. Ross additionally removed Annette Kowalski as the executor of his estate in favor of his wife, whom he’d married a few weeks earlier.
Nevertheless, the Kowalskis sued for control of the Ross estate and won, leading to a flood of Ross-branded merchandise. Ross’s intended heir, his son Steve Ross, sued for control in 2017, but lost the case.