While working a string of odd jobs across Raleigh, Chicago and New York City, Sedaris was discovered reading his diary (which he has kept since 1977) in a Chicago club by radio host Ira Glass, who asked Sedaris to appear on his weekly local program The Wild Room. Sedaris later said, "I owe everything to Ira....My life just changed completely, like someone waved a magic wand." Sedaris's success on The Wild Room led to his National Public Radio debut on December 23, 1992, when he read a radio essay on Morning Edition titled "SantaLand Diaries", which described his experiences working as an elf at Macy's department store during Christmas time in New York.
"SantaLand Diaries" was an immediate success with radio listeners, and made Sedaris what The New York Times called "a minor phenomenon". He began recording a monthly segment for NPR (based on entries in his diary, and edited and produced by Glass), considered adapting "SantaLand Diaries" into a screenplay for Touchstone Pictures, and signed a two-book deal with Little, Brown and Company. In 1993, he told The New York Times that he was polishing his first book, a collection of stories and essays, and had 70 pages written of his second book, a novel "about a man who keeps a diary and whom Mr. Sedaris described as 'not me, but a lot like me.'"
In April 2001, Variety reported that Sedaris had sold the Me Talk Pretty One Day film rights to director Wayne Wang, who was adapting four stories from the book for Columbia Pictures with hopes of beginning shooting in late 2001. Wang had completed the script and begun casting when Sedaris asked to "g[e]t out of it", after a conversation with his sister aroused concerns as to how his family might be portrayed on screen. (He wrote about the conversation and its aftermath in the essay "Repeat After Me".) Sedaris recounted that Wang was "a real prince....I didn't want him to be mad at me, but he was so grown up about it. I never saw how it could be turned into a movie anyway."
In 2004, Sedaris published Dress Your Family in Corduroy and Denim, which hit #1 on The New York Times Nonfiction Best Seller list on June 20, 2004. The audiobook of Dress Your Family, read by Sedaris, was nominated for a Grammy Award for Best Spoken Word Album; the same year, Sedaris was nominated for a Grammy Award for Best Comedy Album for his recording Live at Carnegie Hall. In March 2006, Ira Glass said that Sedaris' next book would be a collection of animal fables; that year, Sedaris included several animal fables in his US book tour, and three of his fables were broadcast on This American Life.
In the March 19, 2007 issue of The New Republic, Outside Magazine editor Alex Heard fact-checked Sedaris's books and alleged that some of what Sedaris described as true events actually never happened. Several published responses to Heard's article argued that Sedaris's readers are aware that his descriptions and stories are intentionally exaggerated and manipulated to maximize comic effect. For his part, Sedaris said he had not read the article, and, of the allegations, stated, "It just bothers the shit out of me."
In September 2007, a new Sedaris collection was announced for publication on June 3, 2008. The collection's working title was All the Beauty You Will Ever Need, but Sedaris later retitled it Indefinite Leave to Remain and finally settled on the title When You Are Engulfed in Flames. Although at least one news source assumed that the book would consist entirely of fables, Sedaris said in an October 2007 interview that the collection might include a "surprisingly brief story about his decision to quit smoking....along with stories about a Polish crybaby, throwing shit in a paraplegic's yard, chimpanzees at a typing school, and people visiting him in France."