Usually appearing glum and annoyed, Robert Klein began his career as a fresh voice for the college crowd. Emerging in the 1960s, while comic icons like Alan King were railing about doctors and airlines, Klein struck a chord with tales of the indignities suffered at the hands of teachers and parents, capturing the misery of being "a child of the 50's." With a sharp and bitter wit, he lamented childhood experiences such as being five and having his mother escort him to public restrooms. Recalling the embarrassment with humor, he quipped, "If I had the moxie to say, 'Relax, lady, I'm only five, I'm essentially impotent, I have no desire for you…' It's humiliating enough to be in here!" Klein's first and best album, "Child of the 50's," was brimming with humor drawn from his own life traumas. From air-raid drills to awkward encounters with a drunken baseball idol, and the confusing narratives spun around historical figures like President Garfield, his comedy was a resonant reflection of the absurdities of the past. He humorously deconstructed the incessant narrative of Garfield’s assassination, quipping, "Garfield was assassinated. Shot by a disappointed office seeker, right? Don't they always say that same sentence? It's crazy. Every time you read his name: James Abram Garfield, 'Shot by a disappointed office seeker…' You look in the Encyclopedia Britannica under Garfield, James Abram. It says, 'See Office seeker, disappointed.'" Born and raised in The Bronx, Klein attended De Witt Clinton High School before heading to the prestigious Yale Drama School. While he initially struggled as an actor, with roles like appearing on Broadway in "The Apple Tree" in the late 60s, Klein found more success in stand-up comedy. During his brief stint with Second City from 1965 to 1966, he honed his comedic chops. Although these were strange times for a newcomer with established comedians dominating the scene, Klein’s style displayed both the caustic bitterness of an Alan King and a unique charm that appealed to younger audiences. As a comedian, Klein navigated the challenging waters between the old-school comics and the emerging counter-culture of comedians like George Carlin. He was too straight-looking for Carlin's counter-culture crowd but too brash for the older generation. Nevertheless, his comedy resonated, marked by pointed one-liners and cartoonish humor. One famous bit involved a hysterical sound portrait of a car trying to start on a cold morning, expertly capturing the motor's desperate plea of "please-don't-try-to-start-me" in a high-pitched "Leave me a-loooooone!" Despite early challenges, Klein transitioned between comedy and acting effortlessly, avoiding television sitcoms but delighting audiences in Broadway musicals such as "They're Playing Our Song," co-starring with Lucie Arnaz. As a frustrated singer, he incorporated comic versions of 50's doo-wop and 60's crooning into his shows, showcasing his diverse talents. The late 70s and 80s saw a blending of audiences, and Klein came to embody the voice of disillusioned hippies-turned-Yuppies and middle-aged audiences seeking relatability. His work, including a talk show on USA cable in the mid-80s, connected with these groups, sharing the frustrations of modern life—from marriage and exercise to the trials of air travel with trademark humor: "On an airplane, order kosher food. Jew and Gentile alike. It throws them into chaos and they deserve that..." Robert Klein’s trailblazing comic style—a blend of sharp social commentary and timeless humor—cemented his place as a beloved comedian who remains relevant across the decades.