1890s to 1910

Part of today's Hollywood Boulevard was called Prospect Avenue, a dusty road that ran through Hollywood towards the neighboring city of Los Angeles. In December 1899, a new railroad construction began to connect Hollywood with Los Angeles in a project that was led by Peter Beveridge, H.J. Whitley, and Griffith J. Griffith.

In May 1900, the railroad connecting Hollywood and Los Angeles was completed, and another one was under construction. In 1901, the Town of Hollywood opened the new macadamized road surface with electric railway that ran down its center between Laurel Canyon and Western. Eventually, the road was widened from 20 feet wide to almost 100 feet wide in some areas.^[4]

In 1903, Hollywood became a municipality, and Prospect Avenue became sometimes called as the Boulevard of Hollywood, albeit unofficially.

In 1910, the town of Hollywood was incorporated into Los Angeles, and Prospect Avenue was officially renamed Hollywood Boulevard.

1920s

In the early 1920s, real estate developer Charles E. Toberman (the "Father of Hollywood") envisioned a thriving Hollywood theater district.^[5] Toberman was involved in 36 real estate development projects while building the Max Factor Building, Hollywood Roosevelt Hotel and the Hollywood Masonic Temple. He partnered with Sid Grauman, and they opened the three themed theaters: Egyptian, El Capitan ("The Captain") (1926), and Chinese.^[6]

1940s–1960s

In 1946, Gene Autry, while riding his horse in the Hollywood Christmas Parade — which passes down Hollywood Boulevard each year on the Sunday after Thanksgiving — heard young parade watchers yelling, "Here comes Santa Claus, here comes Santa Claus!" and was inspired to write "Here Comes Santa Claus" with Oakley Haldeman.^[10]

In 1958, the Hollywood Walk of Fame, which runs from La Brea Avenue east to Gower Street (and an additional three blocks on Vine Street), was created as a tribute to artists working in the entertainment industry.

Decline

In the 1970s, the street became very seedy and was frequented by many odd characters as shown in pictures by photographer Ave Pildas.^[11]

Revitalization

In 1985, a portion of Hollywood Boulevard in Hollywood was listed in the National Register of Historic Places as part of the "Hollywood Boulevard Commercial and Entertainment District". In 1992, the street was paved with glittery asphalt between Vine Street and La Brea Boulevard.^[12]

The El Capitan Theatre was refurbished in 1991 then damaged in the 1994 Northridge earthquake. The full El Capitan building was fully restored and upgraded in December 1997. The Hollywood Entertainment District, a self-taxing business improvement district, was formed for the properties from La Brea to McCadden on the boulevard.^[6]

The Hollywood extension of the Metro Red Line subway was opened in June 1999, running from Downtown Los Angeles to the San Fernando Valley. Stops on Hollywood Boulevard are located at Western Avenue, Vine Street, and Highland Avenue. Metro Local lines 180 and 217 also serve Hollywood Boulevard. A light rail extension station is proposed at the Hollywood Blvd. and Highland Ave. intersection connection the boulevard with West Hollywood, Central LA and LAX.

An anti-cruising ordinance prohibits driving on parts of the boulevard more than twice in four hours.^[13]

Beginning in 1995, then Los Angeles City Council member Jackie Goldberg initiated efforts to clean up Hollywood Boulevard and reverse its decades-long slide into disrepute.^[14] Central to these efforts was the construction of the Hollywood and Highland Center and adjacent Dolby Theatre (originally known as the Kodak Theatre) in 2001.

In the summer of 2005, the city made revamping plans on Hollywood Boulevard for future tourists. The three-part plan was to exchange the original streetlights with red stars into two-headed old-fashioned streetlights, put in new palm trees, and put in new stoplights. The renovations were completed in late 2005.

In the few years leading up to 2007, more than $2 billion was spent on projects in the neighborhood, including mixed-use retail and apartment complexes and new schools and museums.^[14]

In 2021, the Vogue Theater, on Hollywood Boulevard, at Las Palmas, reopened as the Vogue Multicultural Museum.^{[15][16][17][18]}

Renovations of the Hollywood and Highland Center began in 2020. The renovated complex was renamed Ovation Hollywood in 2022.^[19][20][21]

In 2022, for the return of the LA Pride parade to the boulevard, the city installed multi colored lighting to more than 100 trees to illuminate for special events.^[22]