The Carpenters’ Hot 100 Singles Ranked From Worst to Best: Critic’s Picks

The Carpenters may have been the most polarizing pop music act of the 1970s. Karen and Richard had millions of fans worldwide, but also their share of detractors who took delight in mocking their squeaky-clean image. (One jibe, “Goody-four-shoes,” was so clever that Richard got a kick out of it.)

They also personified AM pop music at a time when rock, as well as FM radio, was coming to dominate the music business. They were seen by some as uncool and even corny. And, yes, they released a few singles, “Sing” chief among them, that almost defied their critics to go on the attack. But image considerations fade over time. You have to be of a certain age to even remember when the Carpenters stirred such passions — on both sides of these divides.

Karen and Richard could do no wrong on the pop charts in the first half of the 1970s. They had 16 consecutive top 20 hits on the Billboard Hot 100 at a time when you had to earn each hit one single at a time — unlike in the streaming era, when superstar acts frequently flood the top 20 with multiple hits upon the release of a new album. And they were big around the world: Their greatest hits album The Singles 1969-1973 topped the Official U.K. Albums Chart for 17 weeks, a record equaled by just two other groups or duos (The Beatles and Simon & Garfunkel) in the chart’s 70-year history.

But cracks started to appear in the latter months of 1975. Richard, who produced the duo’s long string of hit, started to wear out. (Jack Daugherty was officially credited as producer in the early years, but Richard made the creative decisions.) Karen developed anorexia nervosa — a then-little-known eating disorder. Nowadays, someone with a similar problem could promptly seek help and feel the love and support of friends and fans. Then, it was held almost as a shameful secret. Karen died from complications from the disorder in 1983 at age 32.

The Carpenters’ reputation has grown immeasurably in the years since her death. Karen is now widely regarded as one of the best female singers of her time. And Richard is increasingly given credit for knowing how to frame that singular voice. Since Karen was so young when she died, it’s nice that Richard has had a good, long life. He turns 80 on Thursday (Oct. 15).

To mark the occasion, here are the Carpenters’ 27 Hot 100 hits, fearlessly ranked from worst to best by an OG Carpenters fan. We show “Superstar” and “Bless the Beasts and Children” as one double-sided single because that it how it’s listed for part of its run on the Hot 100.

We also included one non-Hot 100 hit, “Merry Christmas Darling.” Were we cheating just to get it on the list? Not really. The only reason it didn’t make the Hot 100 when it was released in 1970 is that holiday songs weren’t eligible for that chart back then. (Perhaps it will chart yet, given the annual takeover of holiday hits of all eras under the Hot 100’s current methodology.)

Here’s our ranking. There were only a couple of clunkers destined for the bottom spots, and many classics vying for the top spots.

Grein drew on his liner notes for the 1999 compilation The Singles 1969-1981, as well as fresh research and analysis, in writing this feature.