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My brother, Nick, and I used to compare Jimmy Buffett to Krusty the Clown of The Simpsons. Each guy, we observed, was a popular entertainer who appealed to the masses. But more comical in our eyes was how both the musician and the cartoon character put their names on everything in quest of the almighty dollar.

This was back in the 1990s. Nick liked Buffett’s music whereas I found it to be, well, mainstream beach-party fluff for the unimaginative and un-indie among us. My brother was the smarter guy back then for gleaning Buffett’s appeal.

In 2004, the mom of my girlfriend at the time — a proud Parrothead along with her husband — gave me two Jimmy Buffett CDs: one was Songs You Know by Heart: Jimmy Buffett’s Greatest Hits; the other album was the then-brand-new License to Chill. That’s the record that turned me into a Buffett fan for life.

License to Chill is one of my favorite albums ever. It was heralded at the time of its release as a return to Buffett’s songwriting roots in Nashville, a city where he didn’t leave much of a mark. Buffett recruited several well-known country artists to help with vocals on License to Chill, a great move. I didn’t know until recently that the majority of the songs on the album are covers.

The album’s title might be a playful nod to the Beastie Boys’ License to Ill record from 1986, but whether it is or it isn’t, I don’t think it does justice to the record’s surprising depth. License to Chill contains songs Buffett co-wrote such as the title track, “Simply Complicated,” and “Conky Tonkin,’” tunes that display his sense of humor and fun-loving outlook. But it also has the whimsical “Coastal Confessions,” a song Buffett wrote on his own that is at once autobiographically reflective and lighthearted.

And therein lies the magic of Jimmy Buffett. He’s got his legendary popular tunes, the ones I used to scoff at, such as “Cheeseburgers in Paradise” and “Margaritaville.” Yet some of his biggest hits on that yellow-colored album I received as a gift in 2004 reveal a sensitive, storytelling artist making his way as best he can in the world. Buffett was a fun-loving musical poet.

Listening to Radio Margaritaville on Sirius XM in the morning is an uplifting way to start the day. I’m always amazed at the plethora of Buffett songs on that channel that I’m unfamiliar with. And they always have clever lyrics. Or insightful thoughts. Or goofy observations. Jimmy Buffett was way more prolific, diverse, and talented than I ever imagined him being when I compared him to Krusty the Clown all those years ago. He knows how to pull at heartstrings with what was — I learned after his recent death — a curious, childlike way of looking at the world.

So it turns out Buffett’s personality was the opposite of the hardened and cynical Krusty the Clown, though I will always view Krusty as hardworking and funny, not unlike Buffett. Also like Buffett, Krusty played hard during the off hours. Maybe Buffett found Krusty hilarious too. Maybe they were good friends.

We could use more childlike innocence in this world. Buffett had it, and he possessed a wealth of other gifts. God bless a guy who can sing, laugh, play guitar, drink, joke, smoke, write a book, fly a plane, paint, and open a bunch of hotels. It’s the American way and it’s all proudly for the mainstream masses, many of whom take life too seriously, myself included. I miss him already.