…and ‘A’ Bomb in Wardour Street, by that other band he was in… 
Lake Shore Drive, by the long-forgotten Aliotta Haynes and Jeremiah (the Jeremiah who was not a bullfrog).
“Gun Street Girl” – Tom Waits
“9th and Hennepin” – Tom Waits
“Bourbon and Division” – Firewater (On the corner of Bourbon & Division / Crawling down the crooked streets at dawn… [Although Bourbon St.'s in New Orleans, and the only Division St. I’m aware of is in Spokane, WA.])
South Rampart Street Parade – Bob Crosby and the Bobcats
Real:
Gun Hill Road (Bronx, NY), a one-hit wonder rock group with “Back When My Hair Was Short.”
“Grant Avenue” (San Francisco) – from the musical Flower Drum Song
Fictional:
“Gilbert Street” by Sweet Thursday.
“Boulevard of Broken Dreams”
“Electric Avenue” – Eddy Grant
Dead End Street - Kinks
Slaughter on Tenth Avenue. - various
2400 Fulton Street - title of a Jefferson Airplane ‘best of’ collection, and the address of their former hippie crashpad/band headquarters.
A Tom Petty song “Free falling” mentions Ventura Boulevard (dunno if that’s seperate from Ventura Highway though).
“What’s the Matter Here?” by 10,000 Maniacs. Natalie Merchant sings “We live on Morgan Street…”
Wow! For some reason, I always thought it was Jim Croce!
There’s also a Division Street in Chicago. I don’t know if there’s a Bourbon Street there too.
Ventura Boulevard is a major thoroughfare in the San Fernando Valley, where the song takes place. There is a Ventura Freeway, which could be Ventura Highway, although I’ve never heard that usage and I’m a native Valley Girl. So, no. Not quite the same thing.
Robin
Posse on Broadway (Seattle), Sir Mix-A-Lot
9th at Pine (Portland), Less Than Jake
Pico & Sepulveda, by Felix Figueroa and His Orchestra (contains references to Doheny Drive, Cahuenga Blvd, La Jolla St, Sequoia St, Alvarado St, Santa Monica Blvd, Beverly Drive, and Vine St (besides the title references of Pico and Sepulveda Blvds))
Dylan also covered **Highway 51 ** on his first album.
John Mayall did **Sawmill Gulch Road ** on The Turning Point.
*Arlington Road
Hanover Street*
22, Acacia Avenue – Iron Maiden
I’m a native Valley guy, and I’ve never heard either road referred to as “Ventura Highway” in my life. Maybe it was called that before my time, I don’t know.
Chris Rea’s Road to Hell was written about the M25 (the motorway that goes all the way around London in a big circle).
There’s an old song about 52nd Street in New York (yes, 52d not 42nd - apparently there were and maybe still are a lot of jazz clubs on that street).
Also, I was told about but have never heard a rap number about a street near where I live, Lakeview in San Francisco. If anyone knows this song, please point me towards some lyrics or something?
Ta
Roddy
Church on Cumberland Road – Shenandoah
Carefree Highway – Gordon Lightfoot, who may have been inspired by a stretch of State Route 74 in Arizona
Summit Ridge Drive – Artie Shaw and his Gramercy Five (named for where Shaw lived at one time)
ETA: 52nd Street is by Billy Joel.
Bleecker Street by Simon and Garfunkel.
Zyzzyx Road- a film which is last alphabetically and in box office gross ($30, $10 of which was paid back). Is there a real Zyzzyx Road?