Francis Scott Key
(I mean, who even knows any of his other songs?)
Directly answering “biggest career out of one song” (and not just “biggest one hit wonder”), would have to be Buffet (as a previous poster said).
It’s got a chain of restaurants, margarita mix, tequila, food brand. His company is Margaritaville Holdings LLC
Sure, he had a couple other hits, but “Margaritaville” is an industry.
Come to think of it, he did license “Cheeseburger In Paradise” to a restaurant company, too.
[QUOTE=Full Metal Lotus]
Baltimoria.. Tarzan Boy…
FML
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I love this song. For the longest time, it wasn’t available on iTunes, so I dug up an obscure 80s One Hit Wonders compilation just so I could have it on my iPod.
[QUOTE=Quint]
While not a one hit wonder exactly (due to their no hit status), I’ve always felt that the best example of this is The Violent Femmes. The only album anyone listens to was released in 1982, yet they are still touring based on that album. Of course it is a near perfect “high school angst” album, but 25 years is too long for the angry teen schtick.
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Proof enough of this - I saw them on Late Night with Conan O’Brian sometime in the early 00’s, and they performed BLISTER IN THE SUN!!! BTW, I saw them perform as part of a multiple lineup show in 2001, and they sucked terribly.
[QUOTE=Hypno-Toad]
I have to second Bobby “Boris” Pickett with “Monster Mash.” That thing is dragged out every year for Halloween and force it upon us for commercials and on the radio. It’s not just a one hit wonder, it’s a mandatory one hit wonder.
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True Story - I went to this Halloween Haunt somewhere in Massachusetts when I was in college, which was being advertised as having Boris Pickett as a performer. He did ONE song - Monster Mash! I mean, the guy’s entire career is Halloween songs (It’s Alive is 10x the song that Monster Mash is) so he easily could have done a whole set. I felt ripped off.
The song also gets dragged out for Valentine’s Day and Presidents Day on KBBL 
Henry the VIII wrote Greensleeves. That was pretty much his only hit, and he definitely lived the rock-star lifestyle – scandals, affairs, messy divorces…
[QUOTE=Full Metal Lotus]
Baltimoria.. Tarzan Boy…
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I don’t know if he’s made a career out of it. I remember reading that by the end of the same year this song was released, he went back to work at a gas station.
[QUOTE=denquixote]
Uh, I read the (Norman Greenbaum) wiki link but it does not tell me, what is the second hit?
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By clicking on his name on that page, I discovered that Greenbaum (performing as Dr. West’s Medicine Show and Junk Band) also charted with The Eggplant That Ate Chicago in 1968.
[QUOTE=Finagle]
Henry the VIII wrote Greensleeves. That was pretty much his only hit, and he definitely lived the rock-star lifestyle – scandals, affairs, messy divorces…
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BZZZT–Wikipedia says that is a legend and probably not true.
[QUOTE=Sternvogel]
By clicking on his name on that page, I discovered that Greenbaum (performing as Dr. West’s Medicine Show and Junk Band) also charted with The Eggplant That Ate Chicago in 1968.
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Different name on the 45 counts as a separate act 
. And that song (Spirit in the Sky), which I love, has to be on at least a dozen movie soundtracks in the last ten years.
The lead singer on “Tarzan Boy” (GREAT song) died of AIDS in 1995.
[QUOTE=spoke-]
Francis Scott Key
(I mean, who even knows any of his other songs?)
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Especially since he only wrote the lyrics. They happened to fit an earlier tune composed by one John Stafford Smith.
Iron Butterfly=In the Gadda da vida
One hit wonder that has legs.
[QUOTE=Sternvogel]
By clicking on his name on that page, I discovered that Greenbaum (performing as Dr. West’s Medicine Show and Junk Band) also charted with The Eggplant That Ate Chicago in 1968.
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The follow-up to “Spirit in the Sky,” “Canned Ham,” didn’t quite crack the Top 40. Yes, the Jewish Greenbaum followed his song about Jesus with a song about ham.
I still don’t think anyone has topped Wayne Newton.
He started life as the son of an auto mechanic in Roanoke, Virginia, got a few performing gigs, managed to get one big hit record under his belt (“Danke Schoen”), used that signature song to propel a long-running career in Vegas, managed to parlay that into part ownership of a casino, continues to have a full slate of shows, and now has a major Boulevard in Vegas named for him.
Hard to top. “Danke Shoen” indeed!
Carl Perkins, “Blue Suede Shoes.” The rest are all pikers.
[QUOTE=crowmanyclouds]
Actually there are tons of horror stories about unfavorable contract terms and being basically forced to sell the rights to songs. Very few groups were working during the 70’s and 80’s. Doo-wop concerts are really a “work your elderly ass off” retirement plan, sad really…
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Hence the Paul Simon lyric “Don’t wanna end up a cartoon in a cartoon graveyard.”
All my suggestions have already been mentioned 
[QUOTE=MGibson]
If we can include musical groups how about the Greatful Dead? How many top 40 hits have they had because I can only think of “Touch of Grey.”
Marc
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Six on the Mainstream Rock Tracks.
And six albums went Platinum or better.
[QUOTE=Happy Lendervedder]
Don McLean? I know he’s released other stuff, but shit on a Pringle, he has truly drained the teat with “American Pie.”
And I’m sure someone will come along and name two dozen other songs he’s done, but to most people born in the 70s or later, the only reason they even know this guy’s name is because of “American Pie.” A phenominal song, indeed, but I wager he wouldn’t have one tenth of the career he’s had, nor would he be asked to perform anywhere today, had he not written it.
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Another vote for Don McLean and American Pie. It’s exactly what I was thinking when I opened this thread.
I know he has lots of fans but imagine that your only big hit is only one of the best song ever written.
[QUOTE=spoke-]
In a similar vein, Wayne Newton has built an entire Las Vegas empire on the foundation of “Danke Schön”
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That’s his signature song, but his biggest hit on the singles chart, by far, was “Daddy, Don’t You Walk So Fast.”
[QUOTE=I’m Ron Burgundy?]
Springsteen
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Did you mean Springfield (Rick)? Rick claims they are often confused- my guess is, he gets it waaay more often than Bruce does.