The first Academy Awards ceremony was held here in 1929 — a fact that hangs over the Hollywood Roosevelt like a second architecture, as insistent as the Spanish Colonial Revival tower designed by Fisher, Lake & Traver that rises twelve floors above Hollywood Boulevard. Financed in part by Louis B. Mayer, Mary Pickford, and Douglas Fairbanks, the hotel opened that same year as a gathering place for the industry that was then busy inventing itself a few blocks in every direction. The pool deck visible in these images, ringed by towering palms and low-slung cabana bungalows in warm terracotta tones, was famously painted by David Hockney in 1988 — his shimmering aqueous mural still animating the water's surface. The most recent renovation leaned into the property's accumulated mythology rather than away from it. Guestrooms carry dark iron four-poster beds, tufted brown leather wingback chairs, textured woven rugs, and oak nightstands with recessed drawer pulls — the atmosphere closer to a well-worn private club than to anything produced by a hotel design formula. The restaurant spaces double down on that instinct: herringbone parquet floors, deep mahogany millwork, tufted leather banquettes, pressed-tin ceilings, and a bar lit by an Art Deco drum pendant that throws the bartender into silhouette. The effect is theatrical without being costumed, a calibrated nod to Old Hollywood that the Hollywood Roosevelt has earned the right to make.

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From The Tower, built in 1927, where Gable and Lombard lived, to The Cabanas, vintage 1950s, where Marilyn Monroe lived, guests have two distinct accommodations options. The Tower has undergone a 25 million dollar renovation designed by Yabu Pushelberg. The Tower rooms have larger work desks and are suited for guests traveling on business or with families. The Cabanas are just footsteps from the renowned David Hockney pool and the Tropicana Pool Cafe. The Cabanas are suited for guests looking for an entertaining and lively Hollywood experience.