When Toby Young came to New York City in 1995, the up-and-coming British journalist was, despite his diminutive stature and thinning hair, walking tall and holding his head up high. He’d just been offered a one-month tryout as a staff writer for Vanity Fair and visions of his place at a new Algonquin Round Table were dancing in his head. As might be surmised from the title of Young’s memoir, How To Lose Friends & Alienate People, it didn’t quite work out the way he imagined it.
An Oxford graduate who had been named England’s “young journalist of the year” in 1986, Young cut his teeth working for daily papers in London before establishing The Modern Review in 1991, a scholarly publication that tackled subjects heretofore considered outside the realm of intellectual consideration, such as the popularity of Porkies films in Romania.
The Review attracted the attention of Vanity Fair editor-in-chief Graydon Carter, who called Young out of the blue one day and offered the then 33-year-old Brit a job. Young couldn’t have been more flattered. He’d been a big fan of Carter’s when the latter had been editor at Spy magazine during its heyday in the late 1980s. In Spy’s biting, satirical approach, Young saw evidence of a return to the heady days of Algonquin-era journalism, in which the original incarnation of Vanity Fair, 1914-36, had played a vital role. Now his idol Carter was offering him a job at the prestigious magazine, so perhaps Young shouldn’t be blamed for having such great expectations.
At any rate, Young’s hopes and dreams were diminished soon after his arrival. Possessed with a rapier wit and an equally sharp thirst for drink, he assumed he’d been recruited to churn out humorous, iconoclastic articles lampooning the rich and famous, much as Spy had done during Carter’s reign. But Carter’s days as a publishing rebel rouser, Young sadly discovered, were behind him. The former editor of Spy had become as stodgy and self-absorbed as the celebrities he’d once wickedly satirized.
Try as he might, Young could rarely get more than a chuckle out of his new boss, who continually rejected Young’s wild story pitches, such as the one where he volunteered to go to a neighborhood AA meeting and pop open a can of beer. Young also proved woefully inept at interviewing celebrities, Vanity Fair’s mainstay. During an interview with Birdcage co-star Nathan Lane, Young asked Lane, who happens to be Jewish and gay, if he was in fact Jewish and gay. Lane probably wouldn’t have been so offended if those hadn’t been the first two questions Young asked.
“What were you thinking?” Carter scolded Young afterward. “You can’t ask Hollywood celebrities whether they’re Jewish or gay. Just assume that they’re both Jewish and gay, OK?”
Throughout the book, Young offers inside information on the multibillion-dollar celebrity journalism industry that may startle less cynical readers, such as the fact that only a handful of publicity agents control access to nearly all of New York’s and Hollywood’s A-list celebrities. These agents, not the editors of the various glossy entertainment magazines, determine which writers are given the choice assignments, and scribes who try to buck the system by writing something negative about a celebrity soon find themselves frozen out.
Which is exactly where Young found himself after two unproductive years at Vanity Fair, fired by his onetime idol, Graydon Carter. Young turned to alcohol, and the remainder of How To Lose Friends & Alienate People tracks Young in his descent. Young’s effortless and frequently funny prose is entertaining for the duration of the voyage, from which he somehow manages to extract a happy ending. How To Lose Friends & Alienate People is a hilarious send-up of the culture of celebrity and succeeds in large part because of the author’s willingness to acknowledge, and even embrace, his own numerous failings.