The streets of old Los Angeles come alive in A Bright and Guilty Place, Richard Rayner's non-fiction account of the city at its most corrupt, during the late 1920s and early 30s. The book, which is published tomorrow, borrows a wise-crack description of LA by Orson Welles for its title. It details a group of interconnected characters, some forgotten, others familiar, including attorney-turned-murderer "Debonair Dave" Clark, underworld fixer Charlie Crawford (one of Clark's victims), mobster Albert Marco, crime-scene photographer Leslie White, tycoon Edward L Doheny, and oil industry executive Raymond Chandler, who was observing LA's dark side from the sidelines, collecting material for his future career as perhaps the greatest ever writer of Angeleno crime novels.

Many of the book's key locations can still be found, some in a better state of repair than others, all of them glowing in the refracted light of deeds and misdeeds past. Bradford-born Rayner, who currently lives in Santa Monica, agreed to play tour guide for us, and mapped out a fascinating route from the time-warped boulevards of downtown — LA's once bustling hub — west through Hollywood and Beverly Hills, to the ocean piers of Santa Monica and Venice. Thanks to Rayner's directions and on-site commentary, a forgotten city starts to emerge from the shadow of Tinseltown: a world where actors like Charlie Chaplin have cameos, and the real stars belong to the "LA System": City Hall, the LA Police Department, and Prohibition-era gangland.

For each location, we've recommended a suitable period song.

1. Hall of Justice - currently derelict

Hall of Justice. Photograph: Sally Lohan

Rayner: "So much of the action [in A Bright and Guilty Place] happened in this building, but it's quite hard to find, because it's blotted out by the more recent Criminal Justice Center. You have to seek it out. It was this complete legal city: the towers at the top were the county jail back then, immediately below was the press floor, two floors of courts, and then the DA's office. This is where Dave Clark and Leslie White came to work every day. It was built in 1925, a time when the powers that be in LA imagined they were capable of erecting this grand 'city on the hill'. It was a real nexus of power."

• 210 W. Temple St., Los Angeles, CA 90012

Song: Guilty" by Russ Columbo (1931)

2. Angels Flight Funicular Railway

Angels Flight Funicular Railway. Photograph: Sally Lohan

"As you look out from the top you can see how much of downtown still is from the 1920s. Los Angeles was the fastest-growing city in the world during that decade, and it was all centred here. A lot of the buildings are those you think of as the classic New York type of building: 10-12-storey steel structures, sheathed in brownstone and glass. Here, you get a sense that downtown back then really was this bustling business place. Raymond Chandler fetched up here in 1912, and no other writer really got at the geography and feel and sensuality of the place in the way that he did."

• 351 South Hill Street, Los Angeles, CA 90013 (best approached from Grand Avenue midway between Third & Fourth)

Song: California Blues by Abe Lyman's California Ambassador Hotel Orchestra (1923)

3. Los Angeles Theater

Los Angeles Theater. Photograph: Sally Lohan

"This is where, in 1931, six weeks before Dave Clark shot Charlie Crawford [see 7. The Crossroads of the World], Charlie Chaplin premiered City Lights. It was a huge event, there were crowds outside mingling with the lines of the homeless across the street, and it turned into a bit of a riot. Chaplin invited Einstein, and this was the moment when, with all the crowds mobbing them, Chaplin said to Einstein, 'People cheer me because they all understand me, and they cheer you because nobody understands you.' A lot of the location work in that film was done in downtown LA."

• 615 S Broadway, Los Angeles, CA 90014

Song: La Violetera from City Lights Original Soundtrack (1931)

4. Clifton's Cafeteria - the largest public cafeteria in the world

Clifton's Cafeteria. Photograph: Sally Lohan

"In 1937, someone tried to blow up [cafeteria founder] Clifford Clinton, who had a motto that no one would ever be turned away: in the Depression he was giving food away. A bomb went off in his house, he survived, and the perpetrator turned out to be an LAPD Captain called Earle Kynette — go back in time to 1928 when attorney Dave Clark hit the spotlight, during the trial of a gangster, Albert Marco [see 10. Venice Pier]: Kynette was a character witness, and said Marco was an upstanding citizen, a 'peaceful man'. At a time of very corrupt policemen, Kynette was one of the most corrupt."

• 648 Broadway, Los Angeles, CA 90014

Song: Brother, Can You Spare a Dime? by Bing Crosby (1932)

5. The Bank of Italy Building - former office space, currently empty

Bank of Italy. Photograph: Sally Lohan

"This was the downtown headquarters of Dabney Oil, where Raymond Chandler worked between 1922 and 1932. Chandler was the vice president of the company, earning $12-14,000 a year, drinking a lot, apparently knocking off several of the secretaries. When you see the few pictures of him in the late 20s he was this suave, suited, two-car business executive. He hated working in the oil business. He was an unhappy guy even before he got laid off by Dabney in 1932. So he became a pulp fiction writer, which happened slowly: when he wrote his early pulp stories, he was in his 40s."

• 505 W. 7th Street, Los Angeles, CA 90014

Song: I Guess I'll Have to Change My Plan by Rudy Vallee (1932)

6. The Doheny Mansion

The Doheny Mansion. Photograph: Mike Hodgkinson

"This is all symbolic of the very oldest money in Los Angeles. Owner Edward L Doheny was the richest guy in America, but in the midst of the Teapot Dome [bribery] scandal, his son Edward Doheny Jnr. and his son's chauffeur Hugh Plunkett were both shot in the head. [See 8. Greystone Mansion]. Chandler was obsessed by the Doheny family: [his fictional detective] Philip Marlowe finds himself going into houses like this one. And I know that Dave Clark came to this house — his first job was with a downtown law firm, Wellborn, Wellborn & Wellborn, Doheny's private lawyers."

• 10 Chester Place, Los Angeles, CA 90007

Song: I'm Sitting on Top of the World by Al Jolson (1925)

7. The Crossroads of the World - former shopping mall, currently office space

The Crossroads of the World. Photograph: Mike Hodgkinson

"This is where [underworld fixer and racketeer] Charlie Crawford had his lair. One day in May, 1931, Dave Clark, who was running for judge, came here: Crawford could certainly have delivered the judgeship for Clark if he wanted to, because he controlled rosters of voters. Clark fatally shot Crawford (as well as a journalist, Herbert Spencer, who simply happened to be there), then got into his car, perhaps accompanied by a glamorous blonde getaway driver. A bullet was removed from the wall by Leslie White, one of the DA's forensic people who was investigating the crime scene, taking photos."

• 6665/6671 Sunset Boulevard, CA 90028

Song: I'm Gonna Get You by Ambrose & his Orchestra (1931)

8. Greystone Mansion

Author Richard Rayner outside Greystone Mansion. Photograph: Mike Hodgkinson

"The biggest, darkest, unsolved LA murder mystery happened here, one night in February, 1929. There were two dead bodies on the floor: Edward Doheny Jr. and Hugh Plunkett, the chauffeur. Leslie White, who took the crime scene pictures, arrived at the conclusion that Doheny shot Plunkett, then shot himself. But the plug was pulled and the shutters came down. The splendidly named EC Fishbaugh, the Doheny family doctor, came and pronounced that Plunkett went mad, shot Doheny Jr. and then shot himself. The bodies were buried very quickly without autopsies."

• 905 Loma Vista Drive, Beverly Hills CA 90210

Song: He's a Good Man To Have Around by Jimmie Noone (1929)

9. Santa Monica Pier

"After he shot Crawford, Dave Clark drove all the way west down Sunset Boulevard, before driving downtown. The following morning he came back out here to Santa Monica Pier while he was figuring out what to do. All of this suggests, despite the fact that he bought the gun previously, his shooting of Crawford might not have been pre-meditated. He read in one of the evening papers, right here on the pier, that he had been identified as the shooter. By the time he got to the Hall of Justice, about 30 hours after the shootings, there were scores of press men waiting for him."

• Santa Monica, CA 90401

Song: Between the Devil and the Deep Blue Sea by Cab Calloway (1932)

10. Venice Pier

"At one time, Venice Pier had a famous restaurant called the Ship Café. People would drive there to get the bootleg booze. There was a guy who had come down from Seattle with Charlie Crawford, whose name was Albert Marco, aka Marco Albori, a full-on Italian gangster thug. One night in 1928, there was a fight at the Ship Cafe. Marco shot a guy, and was arrested. The case was given to Dave Clark, who secured a conviction: Marco was sent to San Quentin against all the odds. Clark was the crusading hero, but this is the moment when he started to get involved with bad dudes."

• Washington Blvd & Ocean Front Walk, Venice, CA 90291

Song: Let's Misbehave" by Irving Aaronson & His Commanders (1928)

• A Bright and Guilty Place is available in paperback on 7 January