For years, Van Dyke struggled financially and professionally. He and his first wife, Margie, married on a radio show called Bride and Groom in 1948, in part because the program paid for the ceremony and gave them a free honeymoon. In the late 1940s and early '50s, Van Dyke worked in radio and television in Atlanta and New Orleans. He landed a seven-year contract with CBS in the early 1950s, but was let go after three years.
In 1969, Van Dyke appeared in the comedy-drama The Comic, written and directed by Carl Reiner. Van Dyke portrayed a self-destructive silent film era comedian who struggles with alcoholism, depression, and his own rampant ego. Reiner wrote the film especially for Van Dyke, who often spoke of his admiration for silent film era comedians such as Charlie Chaplin and his hero Stan Laurel. On Larry King Live, Van Dyke mentioned he turned down the lead role in The Omen which was played by Gregory Peck. He also mentioned his dream role would have been the scarecrow in The Wizard of Oz. Twenty-one years later in 1990, Van Dyke, whose usual role had been the amiable hero, took a small but villainous turn as the crooked DA Fletcher in Warren Beatty's film Dick Tracy. Van Dyke returned to motion pictures in 2006 with Curious George as Mr. Bloomsberry and as villain Cecil Fredericks in the Ben Stiller film Night at the Museum. He reprised the role in a cameo for the sequel, Night at the Museum: Battle of the Smithsonian (2009), but it was cut from the film. It can be found in the special features on the DVD release. He also played the character again in the third film, Night at the Museum: Secret of the Tomb (2014).
Van Dyke had four children with his first wife, Margie. The pair lived separate lives for years, before officially divorcing in 1984. The actor became involved with Michelle Triola, an ex-girlfriend of Lee Marvin, in the late 1970s. Trioia had been working as Van Dyke's agent's secretary when they first met. Van Dyke stayed with Triola for nearly 30 years, until her death in 2009. In March 2012, the 86-year-old actor wed 40-year-old makeup artist Arlene Silver.
In 2015 the company paid out $2.5 million dollars in free furniture to 3000 customers after a promotion that gave away the purchases of customers if it snowed three inches each in the cities of Toledo, Fort Wayne, and Chicago. In 2016, Art Van replaced its regional Super Bowl advertisements in the Detroit and Grand Rapids areas with a thank you message for donors of water to Flint, Michigan, which the company had solicited through its charitable programs.