Once upon a time in Hollywoodland

There are a few cultural landmarks everyone knows: the Eiffel Tower in Paris. Big Ben in London. The Taj Mahal. The Pyramids. The Great Wall. But none of them has the charm, the spunk, and the inauspicious beginnings of the “Hollywood” sign, a word that’s become synonymous with Los Angeles and entertainment at large. 

I’ll admit: I may be biased. I’m a working screenwriter.  

I came to Los Angeles in 2015 after a decade in Hong Kong, where I worked at an investment bank, then managed a shipping business, all the while moonlighting as a magazine columnist. But the lasting effect of all this on me was to whisper vague proclamations in my ear about “making it” – so I quit my suit-and-tie job, boarded a Cathay Pacific flight, and ended up in La La Land with a few dollars in my pocket and a head full of ideas.  

It’s not exactly the wide-eyed-country-bumpkin-moves-to-the-big-city rags-to-riches narrative, but hey, reboots always need something modern. And you’d better believe that both bumpkin and I looked up at that big sign below the sky and said to ourselves, “You’re doing it, kid. You’re in Hollywood. The place where dreams come true.” 

As I spoilered to you in the first paragraph, the Hollywood sign did not begin as this monolith of the entertainment industry. It didn’t even say “Hollywood”.   

It said “Hollywoodland”, and was erected in 1923 by publisher and real-estate developer Harry Chandler. His reasons were pure American commerce: it was advertising the name of a new housing development in the hills above LA’s Hollywood district. But he did it in the most showbiz way he could, with giant letters attached to telephone poles illuminated by 4,000 light bulbs. The sign would light up bit by bit: “Holly” then “Wood” then “Land”, then, in all its glory, “Hollywoodland” for the masses to see. 

Just like a film set, the sign was meant to be temporary. Chandler would have it up for 18 months, people would buy into the development, and the sign would come down. But something magical happened: people loved it. The attention it brought, combined with the growing influence of Hollywood in American filmmaking, were the right recipe. By popular demand, the sign remained: it turns 100 this year. 

When I searched for my first apartment in LA, along with the normal civilian concerns – neighbourhood, rent, traffic, safety, greenery, distance from Starbucks – I also had a vocational one: to be able to view the Hollywood sign from my home. Inspiration right out the window! A visual reminder of why you gave up your life in Hong Kong! I put in for a little home overlooking the sign. Harry Chandler’s American commerce thought otherwise, however: I was outbid and had to find other accommodation. But at least I found out that the sign had faced similar financial pressures. And that, boys and girls, is how a screenwriter sets up a transition… 

In 1933, the Great Depression took its toll on both Hollywood and Hollywoodland, and the real-estate project was dissolved. The sign’s new owner decided  that it was too expensive to maintain. And after a decade, the lights literally went out.  

It may have even been for the best, as the sign had been plagued by scandal. The year before, Peg Entwistle, a 24-year-old actress who had left the British stage to pursue a career in film, climbed a worker’s ladder up the letter “H” and fell to her death. This quickly became a national story about the pitfalls of Hollywood: people were coming here to make it– but when it didn’t happen, what were they left to do?

And indeed the Hollywoodland sign reflected these anxieties. In 1944, the letter H was destroyed (stories conflict on if it was vandals or windstorms) leaving behind a very cockney “Ollywoodland”. The rest of the letters were so battered and bruised that residents complained about it as an eyesore and demanded it be demolished. It was only saved in 1949, when the Hollywood Chamber of Commerce entered into a contract with the LA Parks Department to repair and rebuild the sign. Rebuilt it  was, but with the word “Land” dropped: the sign would reflect the district, not the housing development – and the ”Hollywood” sign was officially born. 

After my failure in securing that home overlooking the sign, and during my failures at trying to get a job, I’d spend a lot of time hiking in the Hollywood Hills. It was free exercise and a respite from sitting in a coffee shop surrounded by other wannabe hacks. My favourite hike was what is commonly referred to as the “Mount Hollywood Trail”: four kilometres from Griffith Observatory to the Hollywood Sign. At the end you get a very Instagrammable shot, and another hit of inspiration that you can make it. And unlike having to see the sign from my bedroom window, I could choose when I showed up to see it. 

The Hollywood sign reaches its 100th anniversary this year. It’s had its up and downs, but has still come out on top. As for me, I eventually found my footing as well. I wrote for a little martial arts show for Netflix, then co-created a show for Amazon Asia. I now write and produce one of those crime shows on CBS where we catch bad guys every week. I’m sure there will be more successes too, and plenty more failures. But win or lose, I can always gaze just below the sky, and see a sign that says I’m living in the place where dreams are made: Hollywood. 

5 great things to do in Hollywood 

1. Hike  

Put on your runners and have a go at the Mount Hollywood Trail: Park or get dropped off at Griffith Observatory, then make the four-kilometre hike to the summit of Mount Hollywood. This moderately intense hike offers some of the city’s best views. 

2. Play  

Visit some of Hollywood’s greatest theme parks. Universal Studios , The Wizarding World of Harry Potter (pictured) and more are close by the sign. 

3. Dance  

Hollywood’s famous Greek Theatre and Hollywood Bowl are both nearby for your concert fix. 

4. Drink  

Take in the Hollywood sign as you sip a cocktail from the rooftop of The Dream Hollywood or Mama Shelter (pictured). 

5. Stay  

The Four Seasons Hotel in Beverly Hills and Loews Hollywood (pictured) both feature rooms with views of the Hollywood sign.