November 21, 2025 —– Chart #325
Hello Music Friends,
Hey folks, welcome to another edition of Chart of the Week. Every now and then a song comes along that makes you tilt your head like a Labrador trying to understand a crossword puzzle. If I Had a Boat is that song — a perfectly Texan blend of charm, wit, daydreaming, and “Well now… where exactly is this going?”
Nobody does that better than Lyle Lovett, our lanky, deadpan poet-laureate of oddball Texas wisdom. The man can take a simple idea — having a boat — and within two verses he’s sailing off with Roy Rogers, riding a pony on a boat (still unclear on the logistics), contemplating freedom, loneliness, and maybe divorce law. It’s a journey.
The Song & Recording
“If I Had a Boat” first appeared on Lovett’s 1987 album Pontiac, his second studio record, released when he was still mostly a cult favorite outside Texas but well on his way to becoming the patron saint of clever songwriting.
It was recorded at Chaton Studios in Scottsdale, Arizona — proving once again that Texans will take their music anywhere except Nashville if they can help it.
Pontiac is loaded with studio royalty, and this track includes the wonderful:
- Paul Franklin – pedal steel wizard
- Matt Rollings – piano
- Leland Sklar – bass (yes, the legendary beard himself)
- Russ Kunkel – drums
- Ray Herndon – guitar
Basically, it’s a murderer’s row of session players — the kind of lineup where if you sneeze too loud, someone wins a Grammy.
Chart Performance
This one was never a chart-bustin’ hit for country radio (no surprise there; radio programmers in the ’80s weren’t exactly begging for songs about Roy Rogers and boats that may or may not accommodate ponies).
But it became a signature song, a fan favorite, and one of the definitive Lyle Lovett tracks. You cue up If I Had a Boat, and everybody in the room goes, “Oh yeah… this one.”
So What’s It About?
Well… boats. Ponies. Freedom. Marriage. Cowboys. Being alone. Being with somebody who’d probably fuss at you if you actually bought the boat.
Classic Texas themes.
Lyle once said the song was inspired by childhood daydreaming, but also by a more grown-up fantasy — what life might be like if we could actually do the things we talk about instead of just thinking them. (This is what I tell Debbie when I’m looking at used guitars on Reverb.)
Fun Facts
- Lyle wrote it sitting on the edge of his bed. Which is where most great ideas come from unless you’re Willie Nelson, who writes on the bus at 70 miles an hour with a deck of cards and a roach clip nearby.
- The line “If I were Roy Rogers, I’d sure enough be single” has launched more nervous laughter at concerts than any lyric in the history of Texas.
- Bassist Leland Sklar said Lovett’s sessions were some of the most fun of his career — which is saying something for a guy who’s played on over 2,000 albums.
Playing the Song
This is a great one for acoustic players. The chords are friendly, the tempo is easy, and best of all, the mood lets you drift off into that peaceful “Texas-zen” headspace where you’re thinking, Sure, I could buy a boat…
Of course, you immediately remember the old line:
The two happiest days in a man’s life are the day he buys a boat and the day he sells it.
(My brother Ray may now enter the chat.)
Why It Works
Lovett writes songs the way Mark Twain told stories — with one eyebrow raised. “If I Had a Boat” feels whimsical, but underneath is something deeper and a little wistful. It’s about wanting space. Wanting freedom. Wanting a moment where life stops telling you what you need to be doing.
And that’s why this little oddball song has lasted for nearly four decades. Everybody wants a boat — not for the boating, mind you, but for the possibility.
Keep Rockin’,
Stan Bradshaw