From Portland Afoot
If you've got favorite songs along these lines, post them in the comments or just edit them onto the page.
 The initial list
Our initial list was compiled with help from the anonymous creator of MAXFAQs, Brock Dittus of The Sprocket Podcast and Lillian Karabaic of Portland Afoot's monthly podcast (on which you can definitely expect to hear some of these).
 Young Love (Mystery Jets)
Public transit as romantic lottery.
 Joe Metro (Blue Scholars)
 Handshakes (Metric)
Success, transportational and otherwise, as prison. (See also: Somewhere by Sofia Coppola.)
 North Coast Flyer (Lenny Anderson)
 Beaverton TC (Dr. Something)
"Portland's premier purveyors of post-electric novelty ballads" rhyme "Washington" with "Tualatin" and nearly pull it off. Downloadable here on a name-your-price basis.
 Chillaxin' on the MAX (Dynamix)
 I'm Gonna Be (500 Miles) (The Proclaimers)
 The Bicycle Song (David Rovics)
 You're Crazy for Taking the Bus (Jonathan Richman)
Punk pioneer briefly explains Greyhound.
Though Richman's defining hit was a song about the joys of driving in the suburbs, he's written quite a lot of songs about walkable urbanism, on things like mass transit (The Wheels on the Bus), neighborhood commercial districts (Corner Store), and sterile workplace-only downtowns (Lonely Financial Zone and Government Center.)
 I Missed the Bus (Kris Kross)
Important life lesson from 90s boy genius.
 Light Rail Coyote (Sleater-Kinney)
 I Like My Bike (Hurtbird)
Cake-esque local rockers go commercial ... Portland style.
 Songs added after the initial list
 Civil Twilight (The Weakerthans)
John Sampson's ode to heartbroken Winnipeg bus drivers, submitted by Aaron Brown.
 The Bike Song (Mark Ronson & The Business)
"The catchiest bike song ever," in the judgment of Spencer Boomhower.
 Another One Rides the Bus (Weird Al Yankovic)
The clown prince of musical satire isn't the only weird one on his bus.
 Light Rail (Jeremy Messersmith)
Value proposition for Minnesotans, by Minnesotans: "when the car's too spendy and the bike's too slow." Submitted by Aaron Brown.
 Sounds of My City (Luck-One)
Portland-based rapper Luck-One speaks to the wisdom gained while riding TriMet.
 LDN (Lily Allen)
Early single by the extremely British popstress, about the unexpected pleasures of a suspended driver's license when you happen to live in London.
 Does this Bus Stop at 82nd Street? (Bruce Springsteen)
Springsteen's very first road song was about the exhilaration of joining 1972 New York City's urban mash on the way to see his girlfriend uptown.
 Downtown Train (Tom Waits)
The great promise and terror of public transit: running into your ex in a room neither of you can dash out of.
 Bicycle Race (Queen)
Though it's probably the top-charting song about riding a bike, the title misleads: this is less about racing and more about riding for joy.
 My Bike (Y.N. RichKids)
Fresh off of their runaway viral video "Hot Cheetos and Takis," Minneapolis' youngest hip hop collective speak to their love of their bicycles.
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