Andersen was born in Omaha, Nebraska, and graduated from Westside High School. He graduated magna cum laude from Harvard College, where he edited the "Harvard Lampoon". In 1986 with E. Graydon Carter he co-founded "Spy" magazine, which they sold in 1991; it continued publishing until 1998. While writing for "Spy", Andersen (with Carter) coined the notable insult "short-fingered vulgarian" for future United States President Donald Trump. He has been a writer and columnist for "New York" ("The Imperial City"), "The New Yorker" ("The Culture Industry"), and "Time" ("Spectator"). He was also the architecture and design critic for "Time" for nine years.