[1] After moving to New York City and procuring steady work on radio commercials, Kollmar appeared in the Broadway plays Knickerbocker Holiday (1938) and Too Many Girls (1939).

This episode in Kollmar's career was recalled in a 2016 essay about Waller by John McWhorter, an American academic and linguist who is associate professor of English and Comparative Literature at Columbia University.

... Kollmar's original choice for composer [of Early to Bed] was Ferde Grofé, best known as the orchestrator of George Gershwin's "Rhapsody in Blue," whose signature compositions were portentous concert suites.

During a cash crisis and in an advanced state of intoxication, Waller threatened to leave the production unless Kollmar bought the rights to his Early to Bed music for $1,000.

The evidence suggests, for example, that the standards "I Can't Give You Anything but Love" and "On the Sunny Side of the Street" were Waller tunes.)

Waller came to his senses the next day, but Kollmar decided that his drinking habits made him too risky a proposition for eight performances a week.

[6] From 1945 to 1950, Kollmar portrayed Boston Blackie on the radio program of the same name, a Ziv-produced syndicated series which mostly ran on Mutual Broadcasting System stations.

[7] He also had lead roles in other radio shows including Gang Busters, Grand Central Station and the soap opera Bright Horizon.

[11] Breakfast with Dorothy and Dick was broadcast locally throughout New York City and its suburbs, drawing an audience of 20 million listeners.

[11] In January 1953, the Kollmar family moved from their Park Avenue apartment to a five-story townhouse on Manhattan's East 68th Street,[12] and their radio series began originating from there.

[11] In 1948, Kollmar made his first and only film appearance in the low-budget crime drama Close-Up, directed by Jack Donohue.

[23] In 1958, Kollmar produced The Body Beautiful, a musical about prize fighters starring Steve Forrest, singers Lonnie Sattin and Barbara McNair (in their Broadway debuts), Mindy Carson and Jack Warden.

[24][25] He hired two newcomers, lyricist Sheldon Harnick and composer Jerry Bock, a team who would later write the lyrics and music for the hit shows Fiddler on the Roof and Fiorello!.

In 1952, his gallery called "The Little Studio" opened and was publicized several times by the New York Journal-American where his wife Dorothy Kilgallen was employed.

)[32] In the last months of Kilgallen's life, Kollmar did not have a nightclub or art gallery, was unemployed and his living expenses were paid entirely by her.

[33] Kilgallen died on November 8, 1965, and a year and a few months later, Kollmar opened an art gallery called "the Pastiche" on East 53rd Street in midtown Manhattan.

[34][35] The Sunday edition of the New York Daily News gave it prominent attention, including photos of Kollmar posing with artwork, on February 12, 1967.

"[35] In the spring of 1968, Kollmar and Fogarty purchased the same East 68th Street townhouse where he had lived with his first wife Dorothy Kilgallen and Kerry.

[33] The couple made renovations that included tearing down walls, rebuilding hallways and setting up a studio for Fogarty to design clothes.