In 1890 Victor Ponet, a Belgian businessman and diplomat, bought 240 acres of the old Rancho La Brea. His new estate consisted mostly of poinsettia fields and was just west of a small village that was only just becoming known as Hollywood. Eventually Ponet had a six-hundred foot long dirt road cleared to connect the fields and, in 1921, Los Angeles (which by then had swallowed up Hollywood) used it to extend Sunset Boulevard – named so, according to lore, by ‘mother of Hollywood’ Daeida Wilcox to appeal to potential house-buyers – west to the newly developed community of Beverly Hills. Thus was born ‘the Sunset Strip’.

In this article I’ll give you a brief(ish) history of the Sunset Strip (it’s as racy as you might imagine), and then make some recommendations for things to do, historic sites to visit and some places to eat and drink there (they’re often the same places).

Early History of the Sunset Strip

I’m going tell you a story 

of vice and of glory 

and how it was back in the day. 

The yellow brick road it ain’t, 

it’s the street of sinners, not of saints. 

It’s LA’s Champs De Sleezay.

Mark Mahoney, Sunset Strip (2012)

Almost as soon as it came into being the strip drew the attention of the Los Angeles criminal underworld. Given that it was unincorporated as a city at the time, it was nearly impossible to police as it fell under the responsibility of the Los Angeles County Sheriff’s Department – which was based in downtown, a good nine miles distant.

It was also ideally located between the burgeoning movie-star colonies in Beverly Hills and the Hollywood Hills, and the backlots of Hollywood itself. Soon gambling dens, brothels, bookmaking parlors, speakeasies and all sorts of other places of ill-repute sprang up, run mostly by local mob boss Jack Dragna (who was from Corleone, in Sicily). 

It wasn’t only illegal activity that flourished on the Strip either. In 1932 Schwab’s Pharmacy opened on the corner of Sunset and Crescent Heights. Like many drug stores of that era, it had a meal counter, and it rapidly became an unofficial Hollywood writer’s room, featuring in the noir classic Sunset Boulevard.

Opposite Schwab’s was a legendary hotel, the Garden of Allah, whose complex of twenty-five villas arranged around a central pool at various times housed celebrities such as Errol Flynn, Greta Garbo, F Scott Fitzgerald, Ronald Reagan, Frank Sinatra and Humphrey Bogart.

In 1933 there was a major change when Congress repealed Prohibition. This meant that many establishments along the Strip could go legit and operate out in the open, rather than as password-required speakeasies. And that drew the Hollywood elite in even larger numbers, of course.

Throughout the 1930’s and 40’s, the likes of Judy Garland, Humphrey Bogart, Lauren Bacall, Lucille Ball, Desi Arnaz, Jimmy Stewart, Marylin Monroe, James Dean, Jerry Lewis, Dean Martin, Frank Sinatra, Ava Gardner and Lana Turner were among the galaxy of stars that flooded the nightclubs every night. The most popular were the Trocadero, Mocambo and famous-people-only Ciro’s. 

Very often celebrities would be photographed in these establishments at night, only for their exploits to be seen in The Hollywood Reporter the next day. This was no surprise, since all three clubs were owned by William Wilkerson, who also owned the newspaper, and thus the concept of celebrity gossip, in its infancy at the time, grew into a booming industry.

The Mob Moves In

Meanwhile, the East Coast crime organization known as ‘the Commission’ was looking for a foothold on the West Coast so, in 1937, they sent out a hot-headed young New York gangster named Benjamin ‘Bugsy’ Siegel. Siegel got his nickname because of his infamously violent and quick temper – “crazy as a bedbug”, they said. Of course, anyone calling him that to his face risked serious injury at the very least (he was ‘Mister Siegel’, or ‘Ben’ to his friends). 

Working in concert with Dragna at first, Siegel gradually took over the Strip’s criminal activities, making Siegel the number one figure in the Los Angeles underworld. At that point, he needed muscle and Al Capone’s Chicago Outfit delivered in the form of a short, immaculately-dressed, ex-boxer named Mickey Cohen. Together, Siegel and Cohen ran the rackets in Los Angeles for a decade. Al Capone had been a childhood friend of Siegel’s back in Brooklyn.

Siegel got an easy introduction into Hollywood society, since he’d also been childhood friends with George Raft, a hugely popular Warner Brothers star at the time (often playing gangsters onscreen). In fact Siegel soon became almost as famous as some of his movie-star friends, frequently popping up in the newspaper gossip columns.

His notoriety only increased when he was arrested for murder and, later, illegal bookmaking. The first case was dismissed when two of the witnesses mysteriously died right before the trial (it’s said that one of them committed suicide by shooting himself in the back of the head – twice), and he was acquitted on the second occasion after several Hollywood friends, including Raft, testified in court on his behalf.

One of Siegel’s most profitable rackets was “borrowing” money from members of the Hollywood elite – and then “forgetting” to repay it. Leaving the celebrity in the awkward situation of having to ask the known killer for it back (which of course they didn’t). It’s estimated he made $400,000 from these unpaid loans just in 1938. It’s been said that James Cagney was one of the few stars brave enough to tell Siegel to his face that he wasn’t going to lend him any money. By that time the wire bookmaking business was grossing around $500,000 PER DAY.

Siegel also developed a lucrative sideline in shaking down the Hollywood studios by creating labor issues and strikes with corrupt union officials, which the studios would have to pay him large amounts to avoid.

In the late forties, soon-to-be LAPD Police Chief William Parker began cracking down on organized crime in Los Angeles, making it harder and harder for card games, slot machines, roulette tables, book-making and prostitution to operate out of the back rooms of these nightclubs. So, Bugsy Siegel began looking for a spot a little more suited to his – and the East Coast mob’s – purposes. He found it in a little town called Las Vegas, just over the border in Nevada, a state which had recently legalized gambling. 

Unfortunately, his first (and only) Vegas venture, the Flamingo Hotel, took too long to complete and went too far over-budget for his partners, and Siegel would never see the completion of his vision for an oasis of vice in the desert. He was shot dead in his mistress’ living room in Beverly Hills by unknown assassins, in 1947, leaving Mickey Cohen to run the Commission’s operations in Los Angeles.

Meanwhile, Cohen was so upset by Siegel getting whacked, that he went to the Roosevelt Hotel (opposite the Chinese Theatre in Hollywood) and fired several shots into the ceiling, daring Siegel’s killers to meet him outside. Unsurprisingly, no one appeared and Cohen had to make a quick getaway as the LAPD arrived, but he went on to become the successor celebrity gangster to his deceased boss, appearing in gossip columns and on the new medium, Television. In the mid-1950’s he would do a stint in jail for tax evasion, which finally brought an end to significant mob activities on the Strip.

The Sunset Strip Reinvents Itself

By the late 1950’s, finding it much easier to operate there, most of the nightclubs – as well as the entertainers who performed in them – had drifted east to Las Vegas. Pretty soon Arrowhead Highway began to look identical to the Sunset Strip, and so LAPD officer and businessman Guy ‘String Bean’ McAfee dubbed it ‘the Las Vegas Strip’, a nickname that later became official. 

With the nightclubs and the celebrities gone, the Sunset Strip started to look sleepy and fell into disrepair. It wasn’t until the mid-1960s that a new scene started to move onto it, one that would become indelibly tied to the area.

When Jimmie O’Neill purchased Pandora’s Box at the corner of Sunset and Crescent Heights in 1962, the Laurel Canyon rock scene moved down the hill and onto the Strip, as artists like Bob Dylan, Buffalo Springfield, The Byrds, Sonny and Cher and the Beach Boys played there, drawing a new, younger crowd. When the Whisky a Go Go opened in 1964, the area undeniably became the home of youth and counterculture in Los Angeles. 

There was a problem, though. The residents of the area had not signed up to be the heart of the rock and roll scene and petitioned the city to institute laws against loitering in the area, as well as for a curfew that would limit noise after 10 pm. This tension came to a head on November 12, 1966, when fliers saying “Protest Police Mistreatment of Youth on Sunset – No More Shackling of 14 and 15 Year Old’s” were distributed throughout the neighborhood, announcing a protest that night against the curfew. 

Local rock ‘n roll disc jockeys learned of the protest and broadcast word of it, prompting over three thousand teenagers and young people to flock to the area between Pandora’s Box and Whiskey a Go Go, carrying signs that read things like “Cops Uncouth to Youth!” Among the crowd were the likes of Jack Nicholson, Bob Denver, Dennis Hopper and Peter Fonda, who was hand-cuffed and booked by police in the ensuing brawl. 

The police showed up to enforce the curfew and, while it started as a non-violent protest, events escalated quickly. After a small fight broke out, the event went from peaceful demonstration to violent melee as the LAPD and Los Angeles County Sheriff’s Department tried dispersing the crowd with tear gas and by baton-beating. 

Demonstrators began throwing rocks, overturning cars and smashing windows. The event became known as ‘the Sunset Strip Curfew Riots’ or ‘the Hippie Riots’, and headlines appeared, such as ‘Long Hair Nightmare: Juvenile Violence on Sunset Strip’. Buffalo Springfield, inspired by the events, penned their iconic protest song For What It’s Worth.

Several of the clubs lost their license and went out of business, and Pandora’s Box was acquired by the city council, closed and, ultimately demolished. However, the Sunset Strip remained a bastion of counterculture and the center of LA’s music scene, coming to a climax in the 1980’s and 90’s. 

While heavy metal clubs like the Rainbow Bar and Grill (converted from the Villa Nova Restaurant, site of Joe DiMaggio and Marylin Monroe’s first date, in 1972) hosted Led Zeppelin, KISS, Guns N’ Roses, AC/DC, Metallica, Van Halen and Mötley Crüe, to name but a few. eclectic venues like The Roxy – opened in 1974 by Lou Adler as the venue for the first American run of The Rocky Horror Show – might have Peewee Herman one night and Alice Cooper the next.

As heavy metal gave way to punk, then glam rock, then grunge, the Viper Room opened in 1993, becoming a notorious hangout for celebrities like Johnny Depp, Keanu Reeves and River Phoenix (who met his tragic death there, after overdosing on a cocaine and heroin speedball). 

Our Recommendations

Today you are more likely to see a Starbucks than a movie star and the Sunset Strip is part of the city of West Hollywood, which incorporated in 1984. Posh discotheques and divey rock clubs have given way to corporate logos and luxury housing and many glamorous and decadent places, like the Garden of Allah and Schwab’s Pharmacy, have been bulldozed and disappeared (both were redeveloped in the 1950’s) – as Strip regular Joni Mitchell sang, “they paved paradise to put up a parking lot”.

However, quite a few of the spots that made the Sunset Strip Los Angeles’ favorite place to get in trouble are still around. Here are a few you can check out on your own exploration of the area. 

1. CHATEAU MARMONT

Built in 1929 as an exclusive apartment building, the Chateau Marmont was converted into a hotel in 1931, as the Great Depression made it nearly impossible to find and keep residents. It became a huge success during the 1932 Olympics and its lavishly decorated interior turned it into a hotspot for the Hollywood elite, looking to escape the public gaze.

A studio exec once told a rising young star: “If you want to be seen, go to the Beverly Hills Hotel. If you don’t want to be seen, go to the Chateau Marmont”. The towering facade remains shrouded in mystery, with mischief-seekers flocking to practice clandestine naughtiness on its grounds.

Technically the bar’s only open for hotel guests, but if you go on a slow night and meet a friendly host, you might be able to get a seat. 

2. SUNSET TOWER

Located on the ground floor of the Sunset Tower Hotel, an Art Deco masterpiece, is a bar that was at one point Bugsy Siegel’s Hollywood apartment. John Wayne once brought a cow up to his room, telling his guests that if they wanted milk for their coffee they would have to get it from the source, and Howard Hughes used the penthouse suite as a meeting-place to see his mistresses. In fact it was said at the time that the Sunset Tower was “notorious for having the best-kept call girls in Hollywood”. Allegedly.

3. COMEDY STORE

While an iconic place to visit in its own right, “the world-famous Comedy Store” was once home to Ciro’s, the crown jewel of the nightclub scene during Hollywood’s Golden Age. As the Comedy Store, its stage has been home to Richard Pryor, Robin Williams, Iliza Schlesinger, David Letterman, Jay Leno and a host of other stand-ups. Even today, you can see great comics most nights of the week. 

4. VIPER ROOM, WHISKY A GO GO AND ROXY

You can still see concerts almost any night of the week in these iconic clubs, featuring rising stars as well as headlining favorites from the world of metal, punk, rock, pop and more. So indelibly tied to the music scene are these clubs that, in 2006, the Whisky a Go Go itself was inducted into the Rock and Roll Hall of Fame. 

5. RAINBOW BAR AND GRILL

Decked out in memorabilia from its heavy metal heyday, this place oozes the history of its past. Beginning as the Villa Nova restaurant, a Rat Pack hangout, the upstairs area was famously a home-away-from-home for rock legends like The Who, Alice Cooper, Guns ‘N’ Roses and many more. John Belushi also had his last meal here, on March 5, 1982, before his untimely death at the Chateau Marmont later that same night. 

This map is interactive. To open in Google Maps click the icon in the top right corner.

On the last Saturday of every month we organize a Sunset Strip Tour. It starts at the Chateau Marmont, stops at the Sunset Tower (for cocktails and a great view) and ends at the Rainbow Bar and Grill. Join us for a memorable trip down the Strip.

If you have any feedback on The Sunset Strip: Los Angeles’ Playground please email us or reach out on social media, we’d love to hear from you.

– By Mike Funt (Twitter) and Damien Blackshaw (Twitter)

• Mike Funt is an internationally recognized clown performer and director and Associate Artistic Director of the Clown School. The school organizes classes, workshops and theatrical productions throughout the year, please check their website for more information. He’s also performed many times at the Comedy Store, on the Sunset Strip.