"Sundown" (Gordon Lightfoot)

"Sundown" (1974) by Canadian singer-songwriter Gordon Lightfoot was a song that made frequent appearances on our home turntable.  As a kid, I just enjoyed the song's acoustic groove, which was surprisingly funky for a tune that got significant airplay on "easy listening" radio back in the day.  As usual, I didn't pay much attention to the somewhat mature lyrics.
It wasn't until years later that I really listened to what Lightfoot was singing about: a carousing, unfaithful lover.  Lines like I can see her lyin' back in her satin dress / In a room where ya do what ya don't confess simultaneously leave nothing and everything to the imagination.  (The lyrics are quite the work of literary prowess.)
I also discovered recently that the song is semi-autobiographical.  Lightfoot had been living with a woman named Cathy Smith, a background singer and groupie-extraordinaire who had pretty much been servicing The Band for years before taking up with Lightfoot in the early 70s.  (Years later, she'd infamously give actor John Belushi his fatal dose of heroin and coke in a Hollywood hotel room.)  
Anyway, you might say their relationship was less than idyllic.  One afternoon as Lightfoot was hard at work on music and lyrics, Smith got bored and decided to go out partying with friends, leaving his worried mind to conjure all sorts of scenarios of infidelity as he watched the sunset.
So "Sundown" is the uneasy thoughts of a jealous lover, who comes just short of acknowledging that his relationship with this woman is completely unhealthy.  

"Early Morning Rain" (Peter, Paul & Mary)

When you're feeling lonely or broken, "Early Morning Rain" is the kind of song that reminds you that you're not mewling over your bourbon alone.
Written by Canadian singer/songwriter Gordon Lightfoot in 1964, it's a profile of a guy who is homesick, broke, and full of rotgut.  He's watching planes take off from the airport and wishes that he could hop one like a freight train, hobo-style, to get back home.  
It seems to be a semi-autobiographical snapshot of Lightfoot's stint in Los Angeles in the late 1950s, when he was studying music theory and composition at Westlake College of Music--a time that, by Lightfoot's accounts, was a mix of excitement, lean living, and longing for the familiar.
In an April 2009 CBC Radio interview, Lightfoot recounted to radio personality Jian Ghomeshi that, while he was attending Westlake, he and his classmates often would go watch planes take off at LAX as a no-cost diversion.  One morning, it happened to be particularly foggy and rainy, and the image stuck in his mind, only to pop up years later while babysitting his infant son.
Recalled Lightfoot, "[The image] came back to me, and I wrote that song while I was minding my kid.  I suppose it took me two hours to write the song."
It was after folk trio Peter (Yarrow), Paul (Stookey) & Mary (Travers) recorded the song in 1965 and made it a hit that Lightfoot got offered a management and recording deal, leading to countless others, from Bob Dylan to Elvis Presley, also covering his songs.
As great as Lightfoot's own version is, I prefer Peter, Paul & Mary's take on "Early Morning Rain" because I grew up hearing that version on my parents' copy of (Ten) Years Together, the trio's 1970 greatest hits compilation.  It's the album my parents reached for when I was being a cranky, fidgety toddler.  I must admit, it did a helluva job mellowing me out.  I remember "Early Morning Rain" on vinyl sounding particularly good on my dad's sound system, Yarrow's baritone blending seamlessly with Stookey's tenor and Travers's alto.  The blend was honest and soothing, like analgesic for the brain.  
Incidentally, it was "Early Morning Rain" that came back to me after I'd tentatively moved to Chicago after graduating from college, expecting to land a job writing commercials at one of the many ad agencies that had courted me while I was in school.  
Living frugally on money I'd saved up from working each summer, I pounded the pavement to get interviews with tons of agencies, even going so far as to wait almost 5 hours in the reception area of one behemoth firm, where I refused to let the creative director blow off an appointment that I'd scheduled 30 days before.  (I never did get to meet with one Mr. George Tenney.)
Ultimately, some hiring managers would gush over how funny or creative my work was, and then just never return my calls and emails; others bluntly told me I was a hack.
After getting jerked around for months, hearing empty promises of employment, and then seeing several pieces from my portfolio (including ones that had been derided by junior execs not much older than me) show up on TV with only slight modifications, I bought a ticket and boarded a plane at O'Hare on a rainy morning in August 2000 with $10 left in my pocket.
All I can say is, humming this song in my head helped immensely on the long trek back to North Carolina.