Conan O’Brien, born on April 18, 1963, in Brookline, Massachusetts, is a towering figure in American entertainment, both literally and figuratively. Standing at 6 feet 4 inches tall with his trademark red hair, O’Brien’s comedic style, sharp intellect, and boundless creativity have made him one of the most beloved and enduring personalities in television history. With a career spanning decades, he has worked as a writer, producer, host, and performer, leaving an indelible mark on the comedy landscape. O’Brien was raised in a close-knit, Irish Catholic family as the third of six children. His father, Dr. Thomas O’Brien, is a Harvard Medical School professor and epidemiologist, while his mother, Ruth O’Brien, was a lawyer and partner at a Boston-based law firm. Growing up in a household that valued education and intellectual curiosity, Conan excelled in academics from an early age. He attended Brookline High School, where he served as managing editor of the school newspaper, The Sagamore, and demonstrated an early knack for humor and storytelling. In 1981, he graduated as valedictorian of his class. Following high school, Conan attended Harvard University, where he studied American History. It was during his time at Harvard that O’Brien truly began to cultivate his comedic voice. He joined the Harvard Lampoon, the university’s esteemed humor magazine, eventually serving as its president twice—a rare and prestigious accomplishment. At the Lampoon, Conan wrote sketches and satirical pieces that displayed his emerging style: a blend of absurdism, self-deprecation, and quick wit. He graduated magna cum laude in 1985, ready to pursue his dream of a career in comedy. After graduating from Harvard, Conan moved to Los Angeles to work as a comedy writer. He began his career at HBO’s Not Necessarily the News, contributing sketches and developing his skills in crafting humor for television. His big break came in 1988 when he joined the writing staff of Saturday Night Live (SNL). During his time at SNL, Conan wrote some of the show’s most memorable sketches, including the famous “Mr. Short-Term Memory” and “The Girl Watchers.” His work on SNL earned him an Emmy Award for Outstanding Writing in a Variety or Music Program in 1989. However, after three years, Conan decided to leave SNL to explore other creative opportunities. In 1991, Conan became a writer and producer for The Simpsons, one of the most celebrated animated sitcoms of all time. His tenure on the show is legendary, as he contributed to several classic episodes, including “Marge vs. the Monorail,” which remains a fan favorite to this day. Working with The Simpsons allowed Conan to push the boundaries of comedy, blending sharp satire with surreal humor. His success on the show cemented his reputation as a rising star in the world of comedy writing. Conan’s life changed dramatically in 1993 when he was unexpectedly chosen to succeed David Letterman as the host of NBC’s Late Night. At the time, Cona...