In 1944, as America was emerging from World War II and an unprecedented era of prosperity was dawning, an eleven-year-old boy from tiny Abbott, Texas, put the finishing touches on a homemade book of songs. The front cover made his ambitions clear: “Songs by Willie Nelson,” it reads, in a rough balloon lettering. Beneath that sits the cursive label “Waco, Texas”—even at eleven, the boy from Abbott was dreaming of bigger places, albeit one that was only half an hour away.

The back cover is more clearly the work of a child who was still, in many ways, like any other of his time and place: tiny, hand-drawn cowboy hats adorn the edges, and a whimsical “Howdy Pard” is written in a looping rope script in the center. 

But the contents of the book reflect an understanding of songwriting that extends far beyond the author’s years. Alternating between typed and handwritten pages, this compilation of lyrics, sans musical notation, is filled with songs bearing titles like “Teach Me to Sing a Love Song,” “Only True Love Lingers On,” and “I Guess I Was Born to Be Blue.” Singular in their theme of love, the songs slide between contemplative (“Shinning [sic] with its splendor above / The moon was your helper”) and sobering (“Just remember one thing when your / Wedding bells ring / Only true love lingers on”). That last lyric foreshadows themes that the older Willie would tackle many years later.

Willie’s little book is full of surprising, youthful innovation, and that’s enough to capture any die-hard fan’s attention. But what’s most striking is the songs’ resounding simplicity, which lays the groundwork for the plainspoken, homespun poetry that has been his calling card for three quarters of a century. Musically, no one would dare say Willie’s songs are simple. Supported by a variety of jazz chord underpinnings and his idiosyncratic syncopated singing, they breathe with hints of crooner craft, blues, and swing. It’s almost as if each listener can home in on the style of music that most appeals to them.

But when it comes to words, Willie has doggedly stuck to the American demotic that brung him. “If you can’t say you love me say you hate me,” he wrote in “Undo the Right.” “We gotta all stick together or else I’ll lose my mind,” goes a famous line in “Hello Walls.” “I’m writing a song all about you / A true song as real as my tears” is a sentiment from “Sad Songs and Waltzes” that you can’t quite forget. It’s hard to argue with such perfect simplicity, because out of the simplest language something emotionally complex can emerge—if you’re a master of your craft. “You know this, Robert Earl,” Nashville Songwriters Hall of Fame member Dean Dillon explained when I asked him for some insight into Willie’s songwriting. “The hardest thing to do is write a simple song. Willie wrote ’em.”

When listeners are asked about the first Willie song they heard, many cite Patsy Cline’s 1961 recording of “Crazy,” which is the biggest hit he ever wrote. It’s also, for country music, an unusual song. The first thing one might note is that, like many of his early songs, it has no chorus. There is a pair of verses and a reprise of the second verse that fluctuate with a greater or lesser intensity, and nothing more than a bridge between those first two verses. It’s almost an art song—something you might expect to find in, say, Kurt Weill’s Threepenny Opera—rather than one of the biggest jukebox songs of all time. “Crazy” has fewer than a hundred words in all, and a dozen of them are the titular “crazy,” which is subject to a handful of simple variations. The singer is “crazy for feeling so lonely,” “crazy for feeling so blue,” “crazy for thinking that my love could hold you,” and then, as the words and the melody come tumbling down like bingo balls on a staircase, the song’s crushing close:

I’m crazy for trying and crazy for crying
And I’m crazy for loving you

The word “crazy” appears in eight of the song’s twelve lines. With that degree of repetition one might think a measure of monotony would set in. However, the phrasing that weaves in and out of this relaxed, almost lazy melody is hypnotic. It’s as if the singer and the listener are one as the jeremiad slowly rolls out its melancholy list of woes. The words that make up the song, taken from everyday speech, are easy on the ears—easy enough for a kindergartner to understand. It’s the meaning of the words, taken together, that provides complexity. The emotional context, which stitches the song together, belies the seeming simplicity.

Willie Nelson (left) and fellow songwriter Harlan Howard with their boss Hal Smith, the owner of the Pamper Music publishing company, on July 15, 1961.

Willie Nelson (left) and fellow songwriter Harlan Howard with their boss Hal Smith, the owner of the Pamper Music publishing company, on July 15, 1961.

Jimmy Ellis/USA Today Network

“Funny how time slips away” is one of those Willie songs that echo the sentiments that eleven-year-old Willie precociously captured in “Only True Love Lingers On.” Similar in structure and message, both songs, again, have no chorus and rely on verses that reinforce the hook. It’s an unusual structure, yet “Funny How Time Slips Away” has been covered by everyone from Perry Como to Elvis to the Supremes to Al Green to Dave Matthews. Here, again, it’s the simplicity of the vernacular that undoubtedly resonates with so many. Kentucky’s own red-headed stranger, the singer-songwriter Tyler Childers, says of Willie’s songs, “The thing that sticks is that you never have to reach for a dictionary.”

The song begins with a disarmingly conversational intro:

Well, hello there
My, it’s been a long, long time
How am I doing?
Oh, I guess that I’m doing fine
It’s been so long now
But it seems now, that it was only yesterday
Gee, ain’t it funny, how time slips away

That casual tone, reinforced by the leisurely rhythm of the original recording, is a red herring. It provides a feeling of familiarity; the narrator is talking to someone—an old flame, we soon learn—whom he hasn’t seen in a while. Winsome nostalgia is the underlying mood and is emphasized by the easy, bluesy melody. There’s a slight sense of tension—perhaps there’s a reason the two haven’t spoken in so long—but it’s hardly predominant. The hook line, “Gee, ain’t it funny, how time slips away,” sounds like little more than an anodyne phrase someone uses to fill space in an awkward conversation. However, there’s a dramatic shift in the final verse:

But remember what I tell you
In time you’re gonna pay
And it’s surprising, how time slips away

Suddenly, everything we thought we knew about the song has been upended. Willie tells us that there’s a reckoning coming and there’s no telling when it’ll arrive. The stage lights dim, and this little one-act play of a song comes to a close. Listening to it is thrilling enough, but imagine singing “Funny How Time Slips Away,” feeling its currents subtly shift, collapsing underfoot, while simultaneously realizing that the awkward conversationalist in the beginning is really a cold, calculating bastard. It’s downright chilling.

Willie in the studio circa 1965.

Willie in the studio circa 1965.

Michael Ochs Archives/Getty

Can a song be simple and complex at the same time? Usually, no: simplicity has its pleasures, and so does complexity, and rarely do the two meet. Yet countless Willie songs are among those rare exceptions. The clarity in his songs is crystal, and the vocabulary is straightforward. But it’s not the tail or the snout under scrutiny here; it’s the whole elephant. And that elephant is a tremendous, unadorned, authentic, and complicated wonder. Some might call that simple, but I wouldn’t.

I grew up on Willie and know at least a dozen of his songs by heart. The first song I learned to play on my guitar was “Hello Walls.” I never wanted to be Willie, so when I started writing and performing I clumsily forged my own path. However, because I know so many Willie songs, I’ve often looked to him for inspiration. This is where that troublesome simplicity question comes into play for me. I close my eyes and ask God to ask Willie (they share a condo in Maui) what I should do to get through my writer’s block. I hear a rumble of thunder and then a slow, resounding E chord being strummed, and this message appears gin-clear in my mind: Keep it simple, stupid.

Singer-songwriter Robert Earl Keen, the host of The Americana Podcast, lives with his wife and daughter in Kerrville.


This article originally appeared in the Willie Nelson special issue of
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