Street Musician

A street musician is one who plays an instrument anywhere large numbers of people congregate and/or pass by (such as at a busy streetcorner or subway station) in hopes that people will drop money; usually, his/her instrument case serves as place to gather said money. A common gag is to have the musician be purposely terrible and let people pay him to stop.

Sub Trope of Street Performer, Wandering Minstrel, Super Trope of One Man Band and Organ Grinder.

Anime & Manga

 * Mahou Tsukai Ni Taisetsu Na Koto ~Natsu no Sora~ has Yasuko, who sings and plays guitar across Shitokitazawa station in Tokyo. Main character Sora loves listening to her performances, and Yasuko's songs form a loose commentary on what happens in the series. Yasuko even interacts directly with the main cast later on and is included in the Distant Finale.

Film

 * A violin player is seen playing the old animated Spider Man theme in the second movie.
 * Jamie Foxx's character (a bum who happens to be a virtuoso violinist) in The Soloist.
 * In Zorro's Fighting Legion one of the baddies is a Dreadful Musician mariachi who uses his busking as a cover for relaying secret messages.
 * In Mary Poppins, buskers play back-up during "Supercalifragilisticexpialidocious". Bert also appears as a One Man Band in the opening scenes.
 * There's a street band in Halloweentown on The Nightmare Before Christmas.
 * In Cool Runnings, Sanka tries to collect money for the bobsled team by singing in the street. He only made a dollar and sixteen cents, and most of that came from a man who said, "I'll pay you a dollar...to SHUT! UP!"

Literature

 * The harmonica-player in Moving Pictures.

Live-Action TV

 * One time on Mad About You Paul got some change for a pay phone (remember those?) from a street performer by putting a dollar in the guitar case and taking coins out. He was looked at askance by the performer and passers-by, who thought he was just taking money out. He made a big deal about putting in a five and just taking a little change.
 * Mr. Bean used this trope a few times. Once in the TV episodes he wanted to drop money into a busker's saxophone case but discovered he had no loose change, so he laid down his handkerchief and danced along to the sax music. When a lady walked by and dropped a coin onto his handkerchief, Mr. Bean transferred it into the sax case and continued along on his way.
 * Mr. Bean does some more busking in the 2007 film Mr. Bean's Vacation to several songs playing from a borrowed stereo, culminating in a lip-synched performance of Puccini's "O Mio Babbino Caro."
 * The Monk episode "Mr Monk and the Very Dead Man" concerns a murdered street musician. The other police become convinced that it's the work of a serial killer in the making, one targeting street musicians. So they have Lt. Disher pose as a busker to draw the killer out.

Newspaper Comics

 * Floyd in Beyond The Black Stump, whose playing is so terrible people are more likely to pay him to stop -- even when he's playing air guitar.
 * Little Orphan Annie: Annie worked as this together with "Uncle" Dan.

Video Games

 * Fable 2 - being a street musician (by playing a Guitar Hero-style rhythm game) is one way you can earn money.
 * In Steambot Chronicles, being a busker is a valid choice for making money.
 * In The Sims 1, the first job a Sim in the Music career has is "Subway Musician." Averted in The Sims 2, though; there a Musician sim starts off as a Record Store Clerk. In The Sims 3, anyone who can play a guitar can play for tips, regardless of their job.

Webcomics

 * The buskers in Questionable Content, who even get into a turf war at one point (it's Played for Laughs).
 * In Sinfest, Squidley finds it far more effective than merely begging.

Western Animation

 * There's a Pixar Short called "One Man Band", where a little girl wanting to toss a coin in a fountain to make a wish is accosted by two street musicians, each wanting her coin. They finally make her lose it and she demands to be compensated. They give her a violin, and when she proves to be a virtuoso, someone tosses her a bag full of coins.
 * An episode of Tom and Jerry Tales has Tom and Jerry competing against each other on opposite street corners, performing music for money.