I used to get paid to hang out with famous people

Jonah Perlin, co-founder of Blackbird Spyplane newsletter, describes his twenty-year career as a celebrity profile writer, beginning with a 2010 Rolling Stone freelance contract worth $90,000 annually for 35,000 words of work—a type of arrangement that was rare even then and is virtually unheard of today. He recounts his approach to profiling: seeking sit-down interviews, time in the subject's orbit, and observation of their creative work in progress. He shares specific anecdotes about profiling major figures including Jimmy Kimmel (whom he lived with for three days), Drake (including a visit to a James Turrell art installation), and many others from music, film, and entertainment. Perlin emphasizes that despite the intensity of these relationships, his primary obligation remained to readers rather than subjects, even when this created tension—as exemplified by his Jimmy Kimmel profile that included a marijuana reference which reportedly upset both Kimmel and Disney executives. He describes the gradual decline of the magazine profile business: his Rolling Stone contract was reduced in 2017 after Jann Wenner sold the magazine, then eliminated entirely. The COVID-19 pandemic essentially ended his profile work since the job required in-person access, prompting him and his wife Erin to launch Blackbird Spyplane in May 2020. Though he continues writing profiles for the New York Times Magazine, he now identifies primarily as a newsletter writer. Perlin reflects on how the industry has shifted, noting that many contemporary profile writers have migrated to podcasting, Hollywood, tech, or other fields, while observing that video content is increasingly replacing traditional written profiles at major publications like GQ. He expresses both pragmatic understanding of this shift and nostalgic concern about what is being lost, arguing that video cannot equal the excellence of great written profiles. He notes the irony of becoming a written-word holdout in an era increasingly dominated by audio and video, and celebrates how the current newsletter boom demonstrates that many readers and writers still value this form.