It’s 1967 and your train from Sandusky, Ohio, just rolled into Grand Central. You’ve got a suitcase in one hand and your portfolio in the other. You exit the station and take a right, uptown, before realizing it’s the wrong way. (It’s ok, you’re not from around here). So you turn around, and head down to 223 East 31st Street, the studio of the celebrated designer Herb Lubalin, who was about to give you your first assignment in the big city.

And so begins the career of legendary illustrator Brad Holland — a 50-plus year career that put him on the Mt Rushmore of contemporary American Illustration alongside Milton Glaser, Edward Sorel, Ralph Steadman, Seymour Chwast, and the recently-departed Marshall Arisman.

When you begin your career in the Summer of Love, at some point the conversation is gonna turn to sex. After turning in his first piece to Lubalin’s Avant Garde, a magazine with mild sexual themes, Holland’s next few assignments came from magazines who liked it a little rougher: Screw Magazine and The New York Review of Sex, before finally landing a steady gig at Hugh Hefner’s Playboy.

As Playboy’s legendary art director Art Paul would soon find out, Holland wasn’t like other illustrators. Inspired by Gary Cooper’s Howard Roark in the movie The Fountainhead, who battled against conventional standards and refused to compromise with the establishment, Holland was not willing to execute the spoon-fed instructions given by magazine art directors. He revolutionized the illustrator-for-hire dynamic. It changed everything.

In this episode, Holland talks with our editor-at-large and esteemed design critic, Steven Heller, the co-chair of the MFA Design Department at the School of Visual Arts in New York, an Art Directors Club Hall of Famer and AIGA Medalist, who also calls Holland one of his oldest friends and mentors.

They talk about their early days together, what it’s like to tell your mother that you’ve finally sold a cover illustration—to Screw Magazine (!), how to say NO to a creative director, how to crop an Ayatollah, and—spoiler alert—how to avoid getting mugged in Alphabet City.