Emily has a student, the never-seen, Craig Shumway, who writes all of his essays with song lyrics made famous by different crooners. For his essay, "What Chicago means to me." He writes an essay using the lyrics from two Frank Sinatra songs, "Chicago" and "My Kind of Town". For his essay on Transportation, he uses the lyrics from Dean Martin's "Darktown Strutters' Ball". Emily explains that when he learned she was leaving, he wrote on the chalkboard, "Toot, Toot, Tootsie, Goodbye" by Bobby Darin. And lastly, while in detention, Emily claims he used the lyrics from Frank Sinatra, "One For My Baby (And One More For the Road)".
When Bob's alphabetizing his records, some artists are mentioned; Herb Alpert, Paul Anka, Montovani, and Andy Williams. One album quickly pulled up and put back is the soundtrack of the 1956 film, "Around The World In 80 Days", by Victor Young, which Bob actually putting back upside-down.