Friday Five: Boston

Ken Morton, Jr. | September 21st, 2012

After the Red Sox, Patriots, Celtics and Bruins seemingly won every possible league championship earlier this decade, it was easy to feel jealous of all of those Boston sports fans. Now, the Red Sox have had to overhaul their whole line-up, the Celtics have seemingly passed their window in the NBA, the Patriots are still a threat, but showed cracks in the armor last week against Arizona, and the Bruins might not even play this season. Not even Boston College has a winning record so far in college football season.

Since many of us here at Engine 145 are avid (actually, desperate) fans of some pretty terrible sports teams, we feel your pain. This Friday Five is for you, Boston fans. While your teams might not be the best, celebrate that you are immortalized in some cool songs.

5. Bill Monroe and His Blue Grass Boys – “Boston Boy”

Legendary fiddle player Kenny Baker takes the lead on this classic. Baker played with the Blue Grass Boys from 1957 to 1984, longer than any other band member. He was named to the International Bluegrass Music Hall of Honor in 1999.


4. Kenny Chesney – “Boston”

Back in 2005, Chesney released an album called Be as You Are (Songs from an Old Blue Chair) that included this gem.


3. Carl Belew – “Boston Jail”

“In the county jail in old Boston/They’ve got all kinds, you see/From all walks of life they come/All lost their liberty/Now some got wives just outside/A-waitin’ for their return/Long timers, short timers/And some a-waitin’ to burn.” Porter Wagoner cut the more prominent version of this song, but we’ll go with the great songwriter from Oklahoma here.


2. Willie Nelson – “Please Come to Boston”

This great Dave Loggins hit from 1974 has been covered by David Allan Coe, Joan Baez, Tammy Wynette, Kenny Chesney, Wade Bowen, Reba McEntire, Jimmy Buffett and Confederate Railroad, among others. This one is off of Willie’s 1984 City of New Orleans album.


1. Reba McEntire – “Whoever’s in New England”

This song has some interesting ties. It was written as an answer song to the Barry Manilow song “Weekend in New England,” and Sugarland’s “Stay,” according to songwriter and singer Jennifer Nettles, was written from the perspective of the mistress in “Whoever’s in New England.”


  1. Ben Foster
    September 21, 2012 at 9:07 am

    Never knew all that “Whoever’s In New England” trivia. Now I’m imagining all three songs being performed by their corresponding characters in a big stage musical…

  2. Dave D.
    September 21, 2012 at 9:54 am

    If we’re basing the list strictly on song preference, I’d drop the Chesney song for Uncle Pen, which merits consideration by name checking Boston Boy.

  3. bob
    September 21, 2012 at 10:13 am

    I guessed wrong. Since tomorrow’s the first day of fall, I thought the Friday Five would be about Autumn/Fall songs.

    The following is from Terry Cashman’s Boston Red Sox version of “Talkin’ Baseball”:

    “Boston has tradition
    And with the proper ammunition
    The Sox will fight from April ’til the Fall”

  4. Ben Foster
    September 21, 2012 at 10:34 am

    Bob – From the archives… :)

  5. Jack Williams
    September 21, 2012 at 10:41 am

    Well, there’s the “blue-eyed Boston boy” from the traditional song “The Two Solders,” which has been covered by many. I first heard it on the second album from Norman Blake and Tony Rice.

  6. bob
    September 21, 2012 at 10:50 am

    thanks Ben. Your memory’s better than mine.

  7. Barry Mazor
    September 21, 2012 at 11:15 am

    Well, Peter Rowan and David Grisman are at their absolutely least bluegrass in their late-60s band Earth Opera, which did produce the once famous “The Red Sox Are Winning”–which the Sox and maybe not too many others were:

  8. Arlene
    September 21, 2012 at 2:51 pm

    And then there’s these which also make me think of Boston:

    “Sweet Baby James”- James Taylor
    “Boston”- Patty Griffin (from the unreleased album, Silverbell)
    “When Fall Comes To New England”- Cheryl Wheeler
    “Boston”- The Byrds/Gene Clark
    “Where Everybody Knows Your Name”- Cheers theme song

  9. Rick
    September 21, 2012 at 5:27 pm

    To heck with “Bean Town”! How about something from a grittier area in another eastern seaboard state to the south? I’d pick the Tompall Glaser/Harlan Howard song “Streets of Baltimore” just because it’s NOT about Boston. Well that and the fact Gram Parsons liked the song so much. Go Orioles!

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