Popularity is a strange, strange thing.

Songs that have reached #1 on Billboard’s Top 40 singles charts over the years have shown an astonishing range, from universally loved classics to truly bizarre novelty items.  Witness these two examples:  Aretha Franklin’s “Respect” and Rick Dees’ “Disco Duck.”  Both #1 singles.  Go figure.

If you look, for instance, at just the decade from 1966-1976, the recordings that became (at least for a week) the hottest selling songs in the nation covered an extraordinarily broad spread of genres, styles, tempos, moods and lyrical themes.  Consider these wildly disparate songs:  the garage band rock of “Wild Thing” by The Troggs; the Motown soul of “I Can’t Get Next to You” by The Temptations;  the pop/country/rock mixture of “Black Water” by The Doobie Brothers;  the disco sheen of “Get Down Tonight” by KC and The Sunshine Band; the introspective soft rock of “You’ve Got a Friend” by James Taylor; the country pride of “Thank God I’m a Country Boy” by John Denver; the bubblegum pop of “Sugar Sugar” by The Archies; the mainstream rock of “We’re an American Band” by Grand Funk;  the effervescent British period pop of “Penny Lane” by The Beatles.

See what I mean?  Really great stuff mixed in there with…well, questionable stuff.  It’s a very subjective area I’m getting into here, I realize that.  I’ve never been much of a fan of disco or country, but I loved rock and soul, so what I’m willing to tolerate will obviously reflect those biases.

Today, I want to focus on songs that I call “cringeworthy” — songs that I considered really really bad from the first time I heard them, yet inexplicably (to me, anyway), they reached #1 on the US singles charts.  There are certainly plenty of cringeworthy songs that made it only to, say #8 or so, but here I’m looking at just the ones that somehow topped the charts.  I have even tried to find people that remember EVER liking these, and I have come up empty.  But apparently, someone (a LOT of someones) must have loved them and bought them.  Like I said, popularity is a mystery.

And here are my Top Ten (okay, Eleven) for “Most Cringeworthy”:

“The Night Chicago Died,” Paper Lace, 1974

This song to me has been the proverbial “fingernails on a blackboard” since its day of release.  What were the singers and producers thinking when they recorded it, let alone Peter Callander and Mitch Murray, who wrote this piece of dreck??  Well, dumb like a fox, I guess they say, because the listening/buying audience sent it to #1 for a week in August 1974.  But you don’t hear it in rotation anymore, even on the “crappy Seventies music” station.

“Billy Don’t Be a Hero,” Bo Donaldson and The Heywoods, 1974

Okay, here’s the thing:  These two hacks Callander and Murray, who wrote the previous track, also wrote this one, and the two songs were back-to-back #1 singles here in 1974, but Paper Lace’s version stalled while this version went to #1 instead.  No matter, it’s still awful.  We can all mourn the fact that these two clowns are living in palaces somewhere while far more worthy songwriters continue to struggle.  It’s a disgrace, it really is.

“Something Stupid,” Frank & Nancy Sinatra, 1967

Ol’ Blue Eyes was still relevant but fading fast by the mid-’60s, or so we thought.  He still had serious chops left in him (witness the vibrant “That’s Life” from 1966), but then he’d go and spoil it all by singing something stupid like “Something Stupid.”  Making it worse, he chose to sing this duet love song not with his wife or lover or some worthy female star, but with his daughter, which led some people to refer to it as “The Incest Song.”  Still, it reached #1 here and in the UK, and was actually nominated for Pop Song of the Year (it lost to The Fifth Dimension’s “Up, Up and Away”).

“Convoy,” C.W. McCall, 1976

In the mid-’70s, citizens band (CB) radios were all the rage, which were popular and even necessary for long-haul truckers who needed to stay in touch with each other for their own safety.  Soon, every hot rod and pickup truck had them in their vehicles to communicate the location of police radar traps up ahead.  Naturally, this craze generated a novelty single which, despite its total lack of musical value, reached #1 in January of 1976, and also #1 in Canada and #2 in the UK.  Hey, some people bought pet rocks, too…

“Winchester Cathedral,” The New Vaudeville Band, 1966

For a while in the mid-’60s, we Yanks were somehow enthralled with British dancehall music.  Herman’s Hermits had two big hits with “I’m Henry the Eighth, I Am” and “Mrs. Brown You’ve Got a Lovely Daughter,” and even The Beatles snuck “When I’m 64” onto the otherwise acid-drenched “Sgt. Pepper” LP.  But the most insufferable example of this genre came with this fruity little number from December 1966, which went so far as to use a Rudy Vallee-styled lead vocal that sounded like it was sung through a megaphone.  Rock trivia point:  This band was managed by Peter Grant, who went on to manage heavy blues bands The Yardbirds and Led Zeppelin!

“Seasons in the Sun,” Terry Jacks, 1974

This one has the most interesting history of those on the list.  Written as a French ballad with translation lyrics by poet Rod McKuen, it was recorded first by The Kingston Trio in 1963 and The Fortunes in 1968.  Once The Beach Boys took a stab at it in 1973 and then shelved it, Terry Jacks gave it a pass, and it ended up #1 for three weeks in March 1974.  Are you sitting down?  It one point, it was one of only 40 songs that sold over 10 million copies worldwide!  Come on, it’s awful.  Just awful.  Who ever liked this song?  Raise your hands, I dare you.

“My Ding-a Ling,” Chuck Berry, 1972

I’ve always considered it a travesty, an abomination, that Chuck Berry — the father of rock and roll, the man who invented the riffs that spawned every rock song that followed — had only one #1 song, and it was this silly, awful, live recording of a garbage tune about his penis.  I was a senior in high school when this was released, and I cringed mightily whenever I was with a date in my car and this came on the radio.  Good God, I thought, what has become of the guy responsible for “Sweet Little Sixteen,” “Johnny B. Goode” and “Maybellene”?

“Dizzy,” Tommy Roe, 1969

A bonafide anomaly.  In a year full of revolution, change and fantastic music came this throwback to an earlier time when you could get away with an irritating song like this, with its saccharine-sweet lyrics about puppy love.  But get away with it Roe did, somehow.  It was perched at #1 on the US charts for the entire month of April 1969 (!) and was the top song in the UK and Canada as well.  Please, someone, help me figure out how and why this happened.

“The Candy Man,” Sammy Davis Jr., 1972

This inconsequential piece of fluff was written by Anthony Newley for the 1971 film “Willy Wonka and the Chocolate Factory,” from Roald Dahl’s book.  In that context, for a children’s audience, I have no qualms with it.  But for it to be covered by the likes of Sammy Davis Jr. (who admitted to hating it but recording it anyway), and then hanging out at #1 for an entire month in the summer of 1972, is an appalling lack of judgment by the American buying public.

“Afternoon Delight,” Starland Vocal Band, 1976

Let me just say this sad fact:  This song was nominated for Record of the Year at the Grammys.  Think about that for a minute.  (I’ll be doing another column about the disgrace that is The Grammys in another essay later on.)  Bill Danoff, a member of the “band,” wanted to write a song that “hinted at sex,” and I guess he was successful in that regard, because we often refer now to mid-day hookups as “afternoon delights.”  But musically, this is pretty bad news, I trust you’ll all agree.

“Honey,” Bobby Goldsboro, 1968

This is a no-brainer, for it has appeared on numerous “Worst Songs of All Time” lists over the years.  Its treacly lyrics speak of a man who mourns his dead girlfriend, yada yada yada, and oh my, it’s just one of the most pathetic songs ever to reach #1.  And it stayed there for FIVE WEEKS in April and May 0f 1968.  Unbelievable.  Thank God “Mrs. Robinson” and “Hey Jude” eventually came along to bump it off.

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There are plenty of honorable mentions on my list for the 1966-1976 period:  “The Morning After,” Maureen McGovern 1973; “Island Girl,” Elton John, 1975; “One Bad Apple,” The Osmonds, 1971; “Having My Baby,” Paul Anka, 1974; “Harper Valley PTA,” Jeannie C. Riley, 1968; “Tie a Yellow Ribbon,” Tony Orlando and Dawn, 1973; “Joy to the World,” Three Dog Night, 1971. “Crimson and Clover,” Tommy James and The Shondells, 1969; “The Streak,” Ray Stevens, 1974.

And no doubt there are readers who could come up with plenty of other #1 hits they find cringeworthy that I didn’t include because they’re “guilty pleasures” of mine.  “Close to You” by The Carpenters and “Love is Blue” by Paul Mauriat come to mind…

Warning:  The songs contained on the following Spotify playlist scrape the very bottom of the Top 40 barrel, and may do damage to your ears.  You may need to hit “stop,” “pause” or even “delete” after only 10 or 15 seconds!