Not to be confused with the slightly younger U.S. contractor who was held prisoner in Cuba for five years and released in 2014. Or with the rhetoric professor (1936-2020).

Three of his children's books (from 1978 to 1982) were "Sometimes I Worry," "What If the Teacher Calls on Me?" and "I Don't Want to Go to School Book."

Book covers:

https://archive.org/details/sometimesiworry0000gros/mode/2up
(this is funny)

https://www.thriftbooks.com/w/what-if-the-teacher-calls-on-me-childhood-fantasies--fears-series_alan-gross/2533267/#edition=4300776&idiq=1163791

https://www.amazon.com/Author-Janette-Book-Bundle-Collection/dp/B01NH4Z2SM

https://chicago.suntimes.com/obituaries/2023/9/24/23887872/alan-gross-ad-man-playwright-obituary
(with photo)

Alan Gross, Chicago ad man turned playwright and poet, died Aug. 25 of respiratory failure, according to his wife Norma. He was 76.

Born in Chicago, Mr. Gross grew up in Skokie and attended Evanston Township High School before getting a degree in journalism from the University of Missouri. During his youth, his younger brother Gary Gross said the two bonded over comedy despite their eight-year age difference, adding he was “always learning” something from his “brilliant and intellectual” older brother.

Mr. Gross later went to work for the Chicago-based international advertising agency Leo Burnett. It was at his desk there that he began writing plays, according to Gary, who said his brother told him he couldn’t help but write play scenes between writing commercials.

Shortly after, his 1977 breakout comedy, “Lunching,” debuted to critical acclaim at the Body Politic Theatre before moving to the Drury Lane Theatre and helped the Second City-trained playwright temporarily exit the advertising world.

Even after finding success, Mr. Gross continued attending improv and theater productions around the city and North Shore, including many college productions, his wife Norma said. The couple both pursued artistic endeavors.

“I painted, he wrote,” she told the Sun-Times Sunday. “That’s what life was.”

He never forgot his family either, said his brother, who noted Mr. Gross would always invite him and his mother to screenings and after parties.

Mr. Gross went on to create several more works, such as “The Phone Room,” “La Brea Tarpits,” “The Man in 605,” “The Houseguest,” “Morning Call,” “The Secret Life of American Poets” and the semiautobiographical “High Holidays” — a dark comedy ode to his growing up in Skokie in the 1960s.

“High Holidays” was one of his wife’s favorites because of how truthful it was about real-world issues, Norma Gross said — as well as the fact it was so close to home, with her growing up in different parts of the Chicago area.

She said he would often read his scripts aloud, playing every part as he went down the page, which helped him to do what he often did best — write from every point of view.

“Every character had a part of him,” she said. “He could take all sides of issues going on at the time.”

Dale McFadden, a friend of Mr. Gross who was the artistic director of “Lunching,” agreed, saying his reliance on dialogues rather than monologues is part of what made his writing so enjoyable, along with his ability to portray disappointment so well.

“His curiosity with people is what caused him to write,” said McFadden, professor emeritus of theater at Indiana University.

Mr Gross’ talents weren’t limited to theater, though, as he later wrote articles for Chicago Magazine and the Chicago Tribune in addition to writing children’s books and publishing a number of haikus. He received the Robert Frost Festival Poetry Award in 2008.

Gary Gross said his brother had picked up trombone in recent years, and was “always learning” new things. McFadden called Mr. Gross a polymath for his abilities, adding he had also picked up jazz singing and was a “good packer” whenever the two traveled.

“He just kept going,” McFadden said. “He was full throttle through it all.”

During the last few years while he lived in Old Town, Mr. Gross had been working on more poetry but had broken from the haiku form, “experimenting” with different types. His wife said she plans to publish some of his recent works, whether it be just for his friends or for the public, to “honor his legacy.”

As a more intimate celebration of his life, McFadden said he and Norma Gross had spread Mr. Gross’ ashes at the house they stayed at in Michigan’s Upper Peninsula.

“He had a good eye for the world,” Gary Gross said. “He enjoyed life ... I enjoyed being in his company.”

https://www.youtube.com/watch?v=yxq9h_mXjwc
(4-minute interview from 2009)