Mary Pickford and Douglas Fairbanks, the undisputed royal couple of early Hollywood, bought this hunting lodge in 1919. With the aid of architect Wallace Neff, they transformed it into a mock Tudor royal palace fit for a king and queen. Here they received the blue bloods of the world till their divorce in 1936. Mary lived at Pickfair until her death in 1979.

In 1990, new owner Pia Zadora had the legendary home torn down—she recently claimed it was because the estate was haunted. "You can deal with termites, and you can deal with plumbing issues," she explained. "But you can't deal with the supernatural."

This 1898 Mission Revival mansion was designed by architect John Kremple for the legendary Harrison Gray Otis, editor and publisher of the Los Angeles Times. It was built overlooking the then super-fashionable Westlake Park (now MacArthur Park). After Otis's death, the home became part of the Otis Art Institute before being demolished in 1954. Today it is the site of the Charles W. White Elementary school.

This 1924 Spanish Colonial Revival designed by Wallace Neff was the last home of silent heartthrob Rudolph Valentino, built high in the hills above Benedict Canyon. “What I am dreaming of is to have a home where I could live in peace," he explained. "With a loving wife who would not be wanting to play in film, and who would greet me, each evening, after work, with my children.”

Valentino died suddenly in 1926 and Falcon Lair later became the home of heiress Doris Duke. Many claim that, during the last years of her life, devious employees kept Duke a virtual prisoner in the home. The main house was demolished in 2005.

This low, rambling, Solstice Canyon ranch house was designed by Paul Williams in 1952 for grocery magnate Fred Roberts and his wife Florence. The house was built to accommodate the lush pools, waterfalls, and vegetation on the site.

Roberts's granddaughter remembered the home's beauty: "[Williams] was able to mold the home into the landscape. There was a planter box on the entryway with live trees. The tropical landscaping made it feel like a different area ...The box canyon opened into a wonderland." Sadly, this wonderland was highly flammable, and was destroyed by a 1982 wildfire. Today, you can take a lovely hike up to the ruins.

In 1919, the glamorous actress Alla Nazimova bought this 1913 estate (originally called Havenhurst) and in 1927 she built 25 Spanish-style villas on the property, quickly renting them out to the entertainment community's jet set.

The Garden was home to hard-living luminaries like F. Scott Fitzgerald, Errol Flynn, Humphrey Bogart, Orson Welles, Marlene Dietrich, John Barrymore, Dorothy Parker, and Robert Benchley. One resident remembered, "Nothing interrupted the continual tumult that was life at the Garden of Allah. Now and then the men in white came with a van and took somebody away, or bankruptcy or divorce or even jail claimed a participant ... Nobody paid any mind."

In 1959, the famed property was dismantled to make way for a strip mall. It is alleged that Joni Mitchell's song "Big Yellow Taxi" was written about the Garden's demolition. Today it's slated to become a mixed-use development designed by Frank Gehry.

Josef von Sternberg, famed director of The Blue Angel and Morocco, hired legendary architect Richard Neutra to design this aluminum-clad Modernist masterpiece in the early 1930s. Von Sternberg was one of the first celebrities to build in the then-rural San Fernando Valley. The house was later owned by author Ayn Rand, before it was razed in 1972 to make way for a housing development.

In 1994, Simpson's Brentwood home of 20 years gained international notoriety when it became his last stop in the infamous white Bronco chase that captivated the nation. During his trial, and even after his acquittal, the mansion became a pilgrimage spot for tourists and the media, much to the horror of Simpson's well-heeled neighbors. Simpson lost the home in 1997 after defaulting on the mortgage; the new owner had it torn down the following year. "It's not my house, and I could care less," Simpson told a reporter at the time. "It's part of my past."

The most recent teardown on our list, this 1937 Cheviot Hills house was the home of author Ray Bradbury for more than 50 years. In January 2015, starchitect Thom Mayne began deconstruction of the house, much to the chagrin of Bradbury fans and local preservationists. Mayne claimed, "I could make no connection between the extraordinary nature of the writer and the incredible un-extraordinariness of the house. It was not just un-extraordinary, but unusually banal."

William Andrews Clark Jr. was the son of Montana senator William Andrews Clark, the founder of the LA Philharmonic, and the much older brother of the infamous Huguette Clark. In the 1910s, he bought an ornate mansion in high-class Kinney Heights (today it's Jefferson Park). In the 1920s, he had a pavilion on the property torn down and in its place built a library, where he kept his large collection of Oscar Wilde materials, rare books, and fine prints. The library is now part of UCLA, which tore the adjacent house down in the 1970s because it was seismically unsound.

Hollywood Boulevard was a tourist trap long before its grimy, urban incarnation. In the early 1900s, it was a rural wonderland, with lush gardens and elegant mansions. The most famous of all the estates that dotted the Boulevard was that of the painter Paul de Longpre. In 1901, the noted artist—lured to Hollywood by its founder Daeida Wilcox—built a Mission Revival mansion on three acres of land. The gardens that surrounded the home became a popular tourist destination. The Pacific Electric stopped right in front of the estate, and you could buy prints of popular de Longpre paintings and postcards of the property in the main house. The house was torn down in 1927 to make way for a new kind of Hollywood.

During the 1920s, there was no hotter power couple in Hollywood than the beautiful screenwriter Frances Marion and her hunky cowboy star husband, Fred Thomson. With the help of architect Wallace Neff, the duo transformed an empty hill in Beverly Hills into an enchanted wonderland. "In a short while our hill resembled a gigantic wedding cake," Marion remembered. "Pine trees studded every tier, while on top rose a huge house with a drawing room two stories and a half high, rare tapestries on the walls, an Aeolian pipe organ, and windows overlooking five acres of lawn. Beautifully laid out on the terrace were a tiled barbecue, an aviary, and a hundred-foot swimming pool. Fred and his horses and I had gone Hollywood!"

Sadly, this golden world was short-lived. On Christmas Day 1928, Thomson died in Marion's arms at their home, a victim of misdiagnosed tetanus. Marion immediately put the house up for sale. In 1997, the property was bought by Paul Allen, the co-founder of Microsoft. He soon had everything on the Enchanted Hill torn down.

In 1898, the wealthy Cravens family built a large Tudor-style mansion, designed by Frederick Roehrig, on Pasadena's famed Millionaire's Row. In 1905, beer baron Adolphus Busch purchased the mansion, which was nicknamed Ivy Wall. Over the next few years, Busch would buy more and more land behind the house. On this land he created the first Busch Gardens, a horticultural wonderland that delighted the public for decades. During the '30s and '40s the gardens were sold to developers, and in 1952 Ivy Wall itself was torn down.

This Queen Anne-style mansion was designed by Samuel and Joseph Newsom in 1886. Located on Downtown's Bunker Hill, then the toniest address in Los Angeles, it boasted 35 rooms, five chimneys, and five turrets.

In 1887, mining investor Lewis Leonard Bradbury bought the house. During Bunker Hill's decline it was used by film companies and served as a boarding house for early silent film luminaries, including Hal Roach and Harold Lloyd. Lloyd called the structure Pneumonia Hall, due to its horrible drafts. The ramshackle mansion was finally torn down in 1929.

In 1902, this early Hollywood institution was built by developer HJ Whitley. In 1906, the fascinating heiress Almira Hershey bought the rambling, Mission Revival-style wooden hotel. It became the temporary home of many of the great names in silent Hollywood, including Irving Thalberg, Louis B. Mayer, Ethel Barrymore, Rudolph Valentino, and Norma Shearer. It was torn down in 1956, having long since passed its prime.

This stately Italian Renaissance mansion was built in 1915 as a winter refuge for a wealthy Midwestern family. In 1945, a man named Maytor McKinley bought the house. His widow lived there until the mid-1980s, and after her death, the problems began. A developer planned to tear it down and build an apartment building on the land, so the city declared the mansion a Historic-Cultural Monument. A couple bought the perfectly preserved house and intended to save it by moving it to Chatsworth, but their plans stagnated and the mansion slowly fell into disrepair. People began squatting in the 13,000-square-foot house and in 1994, an early morning blaze destroyed the mansion. The bodies of two transients were found inside.