Phil Leed's third appearance in the series plays a different character. He appeared twice in season 4 in "You Can Go Home Again" and "Quiz Show".
While watching a TV soap opera, Cory says, "Susan Lucci, how do you not win an Emmy?" In 1999, two years after this episode aired, Susan Lucci did win an Emmy for her role on All My Children.
The title is based on the movie/musical "How to Succeed in Business Without Really Trying" (1967). The original Broadway production opened at the Forty-sixth Street Theater in New York on October 14, 1961, ran for 1417 performances, won the 1962 Tony Awards for the Best Musical and Book, and was nominated for Best Score.
Although the name of the TV show Cory watches is never explicitly mentioned, you do hear dramatic, soap-opera-like music and Cory comments on real-life actress Susan Lucci's performance. Susan Lucci stars in the daytime soap opera "All My Children." Both Boy Meets World and All My Children aired on ABC network for the entirety of their television runs.