I’m sailor peg
And I’ve lost my leg
A-climbing up the topsails
I’ve lost my leg
I’m shipping up to Boston
Shipping up to Boston
Shipping up to Boston
To find my wooden leg
The Dropkick Murphys
Firstly, the song was used in Martin Scorsese’s ‘The Departed’, not due to the web of informants but because the events of the film occur in Boston, Massachusetts and the central characters are either Irish immigrants or descendants of the same. The band ‘Dropkick Murphys’ is from an Irish part of Boston. Hence the heavy folk Irish influence in all their music. This song when used as background music is the most Irish sounding song on the soundtrack…besides maybe the bagpipes version of ‘Amazing Grace’. The song combines Irish folk with hard rock to capture the ethnicity and anger of the characters in the movie apart from giving it a very gritty undertone.
Boston has a history of receiving Irish immigrants with the largest mass of immigrants appearing in the 17th and 18th centuries which also has been accounted for in Martin Scorsese’s earlier offering 2002’s ‘Gangs of New York’.
The song is about any Irishman having to sail “I’m a sailor peg” who is “shipping up to Boston”. When that person is on the ship he laments to himself “A-climbing up the topsails… I’ve lost my leg” This represents the fact that he is going to Boston for the same reason many immigrants went to America, for the better jobs, economy and whatnot. The sailor loses his leg metaphorically once he’s on the ship and can’t run anywhere and upon landing on the Americas is fighting for his identity. I mean why the band would make the song about pirates but put a gang in the video. It makes sense because it’s about some guy going to Boston perhaps to join a gang. A lot of the people immigrating were known to be petty thieves or gangbangers in Ireland who were looking for a fresh start in America. Upon landing he is looking for his place in the new world “to find my wooden leg”.
The song is featured twice in the movie and is very symbolic in its positioning.
The first time is when Billy Costigan (Leo DiCaprio) and Colin Sullivan (Matt Damon) decide to and enter into their roles of a mole in the opposing gangs or police respectively. This signifies the sailor getting on the ship. The song is played in a montage sequence where both the lead characters are shown to be behind bars as the viewer watches from the outside and they are beginning the process of infiltration.
The second time the song appears is when both lead characters have reached their psychological and emotional climax and in a single snap of judgment (Colin is shown to pause and think) decide to end their respective undercover allegiances.
Each time the song is used to show a switch in thought, escapism and exploration of other worlds.