There are things each generation must explain to those that follow. Things they must atone for. The Founding Fathers had slavery, for instance. The freewheeling credit spenders of the 1910s and ’20s had the Great Depression. The ”Greatest Generation” had the bombing of Hiroshima and Nagasaki.

My generation has Kenny Loggins.

To be fair, it was actually our parents who brought him his first measure of success, as the ”Loggins” in ”Loggins & Messina.” But they knew what they were doing—L&M’s recorded output, while slight, managed to stay on the sunny side of the line between breezy and banal more often than not. ”Danny’s Song”? ”House At Pooh Corner”? ”Watching the River Run”? Classics.

But then Loggins & Messina broke up, and Loggins proved all too eager to expose himself as the dippy New Age doofus he’d always been at heart. His first few albums were a terrible blend of ponderous mysticism, mush-brained folk, and soft jazz, from the interminably mawkish music to the artwork that seemed to always feature a soft-focus shot of Kenny—all done up in a velour tunic or something similarly lame—striking a ridiculous pose against a backdrop of, say, the universe.

That was bad enough. But then the ’80s dawned, and he discovered two things:

1. He wanted to rock.

2. Synthesizers.

This led to a series of albums, each progressively dumber than its predecessors, on which Loggins managed to pan sacks full of chart gold out of a stream of inane, overproduced drivel masquerading as rock & roll. My generation ate it up—we’re the kids who sent ”Footloose” to Number One—and we’ve never had to pay for it. One day, however, we will have to explain the terrifying success of Kenny Loggins to our children. CAPTAIN VIDEO! does not look forward to that day.

CAPTAIN VIDEO! certainly will not show today’s video to his curious tykes. ”I’m Free (Heaven Help the Man)” represents three terrible musical artifacts from the 1980s—one, it’s a hit Kenny Loggins song from a motion picture soundtrack; two, the portion of the title within parentheses is longer than the portion without; three, in the video, the singer pretends to be an action hero.

This last annoyance was always ridiculous enough when the singer in question was just a simpering soft-rock balladeer (like Peter Cetera in Chicago’s ”Along Comes A Woman” video). But Kenny Loggins has never, in looks or musical essence, given the appearance of someone who would be able to put up a convincing fight against a stiff breeze or a six-year-old girl, let alone a non-quadraplegic adult human being.

And that brings us to the crux of this video’s shittiness: It asks us to accept Kenny Loggins as an escaped convict.

He’s on the run! What did he do to wind up in prison?

Isn’t it obvious? He’s a rebel!

No fence can hold him—especially not when these handy fence-snippers are standard issue for all the inmates!

Will he be able to snip fast enough to get out before George and Stanley find out he’s missing?

In the nick of time, he uses his ninja hippie powers to escape detection!

And…here’s where things get really lame.

Knowing that Kenny Loggins made the least convincing street tough since that time Richie Cunningham wore Fonzie’s jacket on Happy Days, the director had two choices: Ignore it, and try to make everything else as believable as possible, or just bring all the other gangsters in the video down to Kenny’s level.

Guess which option was chosen:

Yes, believe it or not, Poindexter here is the leader of the pack. What kind of town is this? Do the cops even bother carrying weapons? Could the crew keep straight faces while watching the filming of this scene, in which Kenny and Poindexter engage in ”macho” posturing that leaves them both seemingly on the verge of tears?

Of course, Kenny’s come back for his girl. She lives with her parents and doesn’t look to be more than sixteen years old. Kenny, on the other hand, probably left home when Lyndon Johnson was President. Here is where the video turns creepy and crappy.

Ma: What did she say, George? What did she say?
Pa: She’s run off with that damn goodfornothin’!

Pa: (thinks to self) He won’t get far. Can’t run too far on that freak vegan diet of his. I’ll just wait at the county line with a bag of granola and flush him out.

Yep. That’s what I’ll do.

Of course, Pa doesn’t need to go to the county line—the cops have the lovebirds cornered on top of a building in a matter of minutes. Kenny stands around and makes a series of stupid faces while the girl screams and sobs. Looks like it’s back to the hoosegow for Kenny, until who should have a change of heart but…

Yes! It’s Poindexter to the rescue!

On his signal, the town’s troubled, misunderstood youth descend upon the cops, who have no idea what to do. Kenny and his child bride escape. The old ladies in the background clasp their hands to their bosoms and swoon.

This video wasn’t the dumbest thing Kenny Loggins did in the ’80s—that honor belongs to either ”Meet Me Halfway” or his naked wedding to his enema therapist—but it comes close. Painfully close.

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About the Author

Jeff Giles

Jeff Giles is the founder and editor-in-chief of Popdose and Dadnabbit, as well as an entertainment writer whose work can be seen at Rotten Tomatoes and a number of other sites. Hey, why not follow him at Twitter while you're at it?

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