Sullivan had a theater column in Minneapolis at a significant moment of the city's cultural history — the arrival of the Guthrie Theater. Sullivan witnessed and reported the birth of the theater itself, with its innovative design, and the founding tenure of artistic director Tyrone Guthrie.[7]
At the New York Times, Sullivan was a theater and music critic. His focus was off-Broadway, which included for example, his reporting on The Open Theater[8] on the pioneering Cafe Cino, after the death of its founder,[9] on plays by Edward Albee[10] and Lanford Wilson,[11] on a new play that starred Mildred Dunnock,[12] and on a Broadway production of Hello Dolly that starred Martha Raye.[13]
For the New York Times, he reviewed notable productions of Minneapolis, which included plays from the Guthrie Theater, and more experimental fare, including the Firehouse Theater's production of Jack Jack, by Megan Terry. Sullivan noted:
Yes, there is a nude scene in Jack Jack, and it is far more explicit than anything on the New York stage this season. But at the same time, it is so much like a classical painting come to life — of nymphs and satyrs frolicking on the green — that no one in Minneapolis seems to have objected loudly enough to attract the censors.[14]
In 1969 he became the primary theater critic for the Los Angeles Times when theater there was growing. He kept that post for 22 years. At the end of every year he would write a traditional column summarizing theater's highlights, and he would counter that with a humorous column called "Bah-Humbug Awards", which pointed out some low points. Sullivan would end his Bah-Humbug columns with a confession of mistakes that he himself had made during the year.[15]
In Minneapolis in 1961, Sullivan, a journalism professor at the University of Minnesota, joined with Dudley Riggs, a former circus aerialist, and others to create a satirical comedy theater and coffee shop. He wrote sketches and plays to be performed by a cast of actors. Sullivan has said it was "the happiest time of my life ... The companionship was wonderful, and it was great to have a gang and something to enjoy doing as a group. As young people, we were living the business life, most of us as journalists, but we also had doubts about it — sketch comedy and satire proved a release for that."[16][17]
President Ronald Reagan, in 1981, phoned Sullivan, the drama critic of The Los Angeles Times, asking him to give a favorable mention of the musical Turn to the Right, that Reagan's friend, Buddy Ebsen, was starring in. In an article Sullivan quoted the President, who said, "I know this is highly unusual, but I understand Buddy Ebsen has a musical playing out there called Turn to the Right that you wrote a nice review of in the paper. I just wonder if there isn't some way you could let people know that I sure hope it's still playing next time I get home so I can see it." Sullivan said he and the President had a "nice conversation", but that it did become heated. Sullivan replied to the president, "I'm ashamed of you. Here you go around cutting the arts programs, and now you go around plugging a show." The President answered, "I'm rather sorry you feel that way." They went on to discuss how arts programs were funded. Reagan mentioned "boondoggles" that were funded by the National Endowment for the Arts, such as one word poems, and performances staged in laundromats. Sullivan pointed out that there were multi-billion dollar boondoggles in the defense department budget, and the President concurred. The budget for the arts endowment that year was about $165 million. Sullivan mentioned that his original review was not a rave. "It's a pleasantly engendered nostalgic musical that didn't sustain the mood because it was so badly put together," he said. "You can't totally hate it. It's harmless. But you can't constantly eat peach ice cream in the theater without getting sick on it."[18][19]