John Mellencamp feat. India.Arie – “Peaceful World” – (2001)

One of the purveyors of musical Americana had this minor hit in the aftermath of 9/11. The song was actually around prior to the attacks, but it really picked up steam afterwards – although it never officially charted, bubbling under at #104. Also, Mellencamp’s face is way too airbrushed on that album cover. Right?

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John Mellencamp & Me’Shell Ndegeocello – “Wild Night” – (1994)

Covering a Van Morrison song is always a risky proposition as he is amazing. But the man formerly known as John Cougar Mellencamp – with help from singer Me’Shell Ndegeocello – really knock this one out of the park. The song has a funky feel to the bassline and pretty sweet guitar. It was a big hit too, topping out at #3 on the Hot 100 and #1 on the Adult Contemporary chart.

John Mellencamp – “Again Tonight” – (1991)

This could have totally been the b-side for “Hurts So Good.” Sorry, Mr. Mellencamp, but your sound hasn’t evolved all that much in the past 30 years. This was a #1 on the Mainstream Rock chart, but it only hit #36 on the Hot 100. It’s not that rock-y that I feel it would’ve performed better on one chart over the other, but it was 1991, and things were weird.

John Cougar – “I Need A Lover” – (1979)

This was John Mellencamp – er, John Cougar’s first big single and it was released off the album that shares its title with the song in 1979. It peaked at #28 on the Hot 100 in 1979 but continued to receive airplay throughout the 80s and still to this day. It is associated with the 80s to me because I associate John Mellencamp with the 80s. What’s interesting about this song is the instrumental intro that runs for about two and a half minutes. If you’ve ever heard radio DJs talk over the usually short intros of songs and stop talking just as the lyrics begin (this is called “hitting the post”). Well, this song is their worst nightmare. Try to fill 150 seconds – exactly – with random gibberish. It’s not easy.

John Mellencamp – “I Saw Mommy Kissing Santa Claus” – (1987)

This is easily the best version of this song. Mellencamp really takes a 1950s Christmas standard (kinda) and rocks it. This was another radio-friendly Christmas hit from the first charity album A Very Special Christmas (there are a series of them) that benefitted the Special Olympics. The other big hit from this was Bruce Springsteen’s “Merry Christmas Baby.”

This song has a very country-rock feel to it. It’s like a hillbilly orchestra going on in the background. Someone is clearly playing the cow-bell and I’m pretty sure that’s a banjo… in a Christmas song? Very cool.

John Cougar – “Hand to Hold On To” – (1982)

This was the third track and the third single from American Fool and considering that it followed up both “Hurts so Good” as well as “Jack & Diane” it really never stood a chance. It flew under the radar in 1982 and still does. I’ve heard it on the radio, but not with the same frequency we get other Mellencamp hits. It’s still decent and very early-80s-Mellencamp.

John Cougar Mellencamp – “Cherry Bomb” – (1987)

The Lonesome Jubilee was Mellencamp’s fifth album in the 1980s. “Cherry Bomb” is very similar to “Jack and Diane” in that it’s a nostalgic song about past relationships. But unlike songs like “Pink Houses” this one is upbeat, generally, and happy. I just realized that almost every John Mellencamp song is fundamentally the same: a longing look back at some slice of Americana.

John Cougar – “Hurts So Good” – (1982)

This was a serious contender to make the list and at the last second I substituted “Pink Houses” in for it. I like this one better… but man, if there was ever a music video that can really ruin a song for you, this is it. Why is he wearing a leather shirt, bandana and chaps? Man, the 80s were weird.

John Cougar – “Jack and Diane” – (1982)

This is one of the biggest songs of the 80s – I chose “Pink Houses” for the countdown because this seemed too obvious, but in reality this was a far bigger hit and far more important in 80s music and the career of John Mellencamp, who at this time was going by John Cougar. It was his biggest hit – a #1 for four weeks in the fall of 1982. Jack and Diane became defining characters of the 80s. Everyone knows who they are and everyone knows about the Tastee-Freez. This song oozes nostalgia about American youth – a theme throughout most of the Mellencamp catalog.

#67 – John Mellencamp – “Pink Houses” – (1983)

John Mellencamp was one of the most successful and popular artists of the 1980s, singing about Middle America and everyday life and all of that. This is the song that most exemplifies the whole “average American thing,” for he says things like, “Ain’t that America, you and me…” etc. This song was featured on 1983’s Uh-Huh along with the also good “Crumblin’ Down” and “Authority Song.” It made it to #8 on the Hot 100 – and yes, this is the Mellencamp entry on this list. No “Jack and Diane” here.

#14 – Bruce Springsteen – “Merry Christmas Baby” – (1989)

A Very Special Christmas was an album put together to benefit the Special Olympics. The Boss’s “Merry Christmas Baby” is tops on the album (barely) – mostly because of the raging saxophone and the belted lyrics. There is a short instrumental intro and then Bruce does a little talking building to it, then at about the 1:07 mark he lets loose the title of the song – which is one of the most rewarding moments in song. Bruce also did quite a famous version of “Santa Claus Is Coming to Town,” and don’t forget to check out B.B. King’s bluesy version of “Merry Christmas Baby.” A Very Special Christmas had a string of other hits as well. There was the Eurythmics somewhat irritating version of “Winter Wonderland” and Bob Seger’s okay version of “The Little Drummer Boy.” But I think the real gem of the album is John Mellencamp’s rockin’ version of “I Saw Mommy Kissing Santa Claus,” which even if it had different lyrics, it would still be an awesome song. The music just rocks.