The most famous sign in the world turned 100 in 2023. Sort of.

Funnily enough, the hyperbolic part of that opening sentence isn’t the reason for the caveat – for nobody can mount a convincing argument against the Hollywood sign being the most widely known of its type on the planet. The closest competition resides in the adjacent state but ask a thousand people to name a sign and I guarantee that Hollywood will recur far more frequently than Welcome To Fabulous Las Vegas. (Which is itself a fine and worthy contender; we’re just talking about an all-timer here, a veritable icon. The Don Bradman of signage. When it comes to public display of symbols, nobody does it better than those nine white letters on the Santa Monica mountains.)

No, the funny thing about the Hollywood sign is that for the first 26 years of its existence it didn’t spell Hollywood but Hollywoodland, the name of a housing development in the Hollywood Hills newly constructed in 1923. To advertise this new development, some enterprising souls paid $21,000 for its name to be spelled out in gigantic letters on the crest of Mount Lee, overlooking Los Angeles. Measuring approximately 43ft by 30ft, these letters were electrical and flashed ‘Holly’ ‘Wood’ ‘Land’ into the Californian night – benefiting not only the developers but also local suppliers of curtains and blackout blinds.

Although the sign outlasted its intended 18-month lifespan, the early years were not auspicious. In 1932, struggling British actress Peg Entwistle committed the most on-the-nose suicide of the 21st century by launching herself off the H. Then the Great Depression bankrupted the Hollywoodland development and the sign was sold to the city in 1944, the same year the H fell down, causing the sign to perform history’s first Michael Caine impression with the great man still only nine years old. “Welcome to ’ollywoodland.”

The old Hollywoodland sign

In 1949, the ‘H’ was restored and the ‘land’ removed; ‘Hollywood’ finally emerged. Yet its travails were not over. Time was unkind: arsonists set fire to the second ‘L’, an ‘O’ fell down the mountain. A saviour emerged in the unlikely form of Hugh Hefner, who hosted a 1978 fundraiser at the Playboy Mansion in which Hefner and either other donors paid $28,000 to each fund a new letter. Alice Cooper was among the eight, the rock star buying the ‘O’ in honour of Groucho Marx. Hefner got the ‘Y’; perhaps ‘H’ was too obvious.

The sign has subsequently been destroyed multiple times – but only in the movies. You should be safe to take one of the several hiking trails that lead up to the sign. Be warned: the view is too immense to capture on a camera phone. In the foreground the green slopes of Griffith Park and the mansions scattered amid the trees; beyond a boundless gleaming smudge of blue and silver stretching so far into the horizon it seems to become part of the sky. Brooding in the distance the silent silhouettes of Downtown LA might almost be a mirage. Without wanting to get too cute, I suppose the big white sign behind your shoulder has played a similar trick on millions of people staring in the opposite direction.

The Hollywood sign

For a few, of course, the sign was not a mirage but a promise. Walk along Hollywood Boulevard and count the stars on its Walk of Fame – 2,768 at the time of writing. (OK, maybe don’t count all of them.) Even better, head to Grauman's Chinese Theatre and compare your handprints to those of numerous cinematic legends imprinted in concrete across its forecourt. The earlier imprints often include personal messages to Sid Grauman, founder of the Chinese Theatre. The Dolby Theatre, host of the Oscars, is right across the street.

There’s a famous quote about Los Angeles: “72 suburbs in search of a city.” Some attribute it to Dorothy Parker, others to Aldous Huxley. Whatever, the sentiment rings true: LA isn’t a unified metropolis so much as multiple different areas with their own characteristics, culture, even climate. The sun can shine over Beverly Hills while mist and drizzly covers Venice Beach. You can’t really do LA in one visit, unless you’re visiting for a month. Wise visitors will focus on a few of those 72 suburbs and do them properly. Wiser yet, build your trip around a theme: food, art, bars, beach. In LA, you can find pretty much anything.

Our trip was based around the movies. We hiked up to the sign, strolled down the Walk of Fame, even toured a studio – Warner Brothers in our case, although other studios are available. Studio tours are very touristy and, like many very touristy things, actually quite fun. You are chauffeured in a buggy between soundstages the size of space stations. Inspect miniature towns of fake trees and empty houses – some of which played starring roles in your adolescence. There’s the staircase where Ross failed to ask Rachel to prom. There’s the actual Friends sofa. Yes, you can take a photo. Friends was entirely shot on the Warner Bros backlot; the cast never filmed a scene in New York.

Central Perk Cafe at Warner Bros Studio

In a way, LA is one gigantic studio: screen history is everywhere you look. The most famous highway in the city, Sunset Boulevard, shares a name with one of Hollywood’s greatest films. The movies may have got smaller but the town remains as alluring as ever. Walking down Sunset, I stumbled upon a tiny bookstore – Mystery Pier Books. Its shelves were crammed with rare prints and first-edition classics signed by their authors; its walls bore photographs of the countless celebrities who have stopped by.

The website shares their testimony: “I love this shop!” proclaims Guillermo Del Toro. Jude Law “died and went to heaven.” Daniel Craig “could spend a lifetime here.” Angelina Jolie calls it “a dream.” Flea believes Mystery Pier to be “the best bookshop in the world.” Founder Harvey Jason was a prolific actor himself, notably playing the hunter in The Lost World: Jurassic Park. Harvey’s there most days and more than happy to share some stories. I couldn’t afford a first-edition but I bought a Mystery Pier T-shirt, which puts me in storied company. I wear it whenever I need to look cool.

Those seeking stars of a different kind should head up to Griffith Observatory on the slopes of Mount Hollywood. There you can enjoy phenomenal views of LA, the Hollywood sign and the planet Jupiter (or whatever planet happens to be visible at the time – we got Jupiter). Naturally, there are movies: 35 minute animations playing in the Planetarium theatre on vast Imax screens. Explore the cosmos, witness the creation of life itself. Relax into the stunning, frequently trippy visuals and the incredibly soothing live narration. Apropos of nothing, marijuana is legal here.

View from Griffith Observatory

Like every Hollywood destination, the observatory has appeared in multiple films, typically when an astronomer needs to spot an encroaching asteroid or alien spaceship. However its most famous appearance comes in the 1955 James Dean classic Rebel Without A Cause, where it hosts the most picturesque knife fight in cinematic history. A bust of Dean stands in the grounds; he died in a car crash the year of the film’s release.

At least one In-N-Out burger is a must: don’t forget to go animal style from the secret menu. Speaking of secrets… The Magic Castle is a private members club and you’ll either need to be invited by a member or stay at the adjacent hotel. Dress code is formal, a tie is mandatory. Photography is banned. The food is great but expensive, even by LA standards. The evening is unforgettable.

Magic is quite literally everywhere: performed on stage, at the bars, in the corridors. The whole venue is a kind of time machine, transporting you back to another, more glamorous era than this one. But then that’s Hollywood all over, isn’t it?

Mama Shelter

Mama Shelter Room

Regular readers will know about our ongoing devotion to the Mama Shelter, the super stylish hotel brand that launched in 2008. Since that Parisian opening, a total of 18 different Mamas have opened around the world. Something is going very right indeed. What’s the secret? Relaxed atmosphere, assimilation into the area, and incredibly cool wallpaper, to name but three.

Mama Shelter LA is the only American Mama at the time of writing. Like its European cousins, the hotel has a packed itinerary of events and activities to ensure guests are never bored. Fancy an evening of drag queen bingo – aka bingo hosted by a drag queen? Mama’s got you. At a loose end of a Friday evening? Head upstairs to the Mama Does Fridays Better rooftop party and get your jam on with food, drinks and a live DJ.

About that rooftop: Mama Shelter LA boasts some absolutely stonking views. The Hollywood sign is directly in your eyeline, downtown LA spreads beyond the rooftops. The helicopters that frequently patrol the sky only add to the cinematic nature of the scene. Needless to say, golden hour is a little bit special.

Mama Shelter Roof

The location is a doozy, bang in the middle of West Hollywood. You’re a block away from the Walk of Fame; a 15-minute cab ride removed from Griffith Observatory and the studios. Mystery Pier Books and Beverly Hills will take the same amount of time on the bus. Most importantly of all, you can walk to your nearest In-N-Out on Sunset Boulevard.

However you cannot live off In-N-Out alone (please don't try). Fortunately the hotel restaurant downstairs serves a homemade menu of delicious dishes that combine American classics (e.g. Braised Short Ribe) with more exotic fare (New Zealand Tai Snapper, anyone?) Food – and numerous cocktails – are also available on the rooftop.  

As always with Mama, the rooms are spacious, quirky and extremely comfortable. If you can, request the Jimi Hendrix room. He allegedly stayed there in the hotel’s previous incarnation; the door is purple and there’s a guitar on the wall. You won't become a rock God overnight but you might just feel like one – and that's half the battle in this town. 

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For more info, see Mama Shelter and Discover Los Angeles