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John Mellencamp Greatest Hits: 15 of The Legend’s Top Tracks

Check it out: We’ve rounded up the small-town rocker’s most impressive tunes! 

Though he’s not so fond of critics calling him “the voice of the heartland,” John Mellencamp isn’t going to complain about it either. “In some ways, you take what you can get. So I’ll take [it]. But that’s not how I see myself,” Indiana’s famed rocker once told Esquire.

Either way, the artist has never turned his back on his small-town roots in Seymour, often singing about both the joys and struggles of America’s midwest and other parts of the country that are far from the bright lights and big cities on the coasts. And in 1985, he even co-founded the Farm Aid benefit concerts with Willie Nelson and Neil Young.

“Small family farmers are what made this country what it was,” Mellencamp told CBS News. “When I was a kid all of these small towns across America were supported by farming. There was a saying, the way the farmer goes, goes America. And that has changed dramatically.”

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man standing with hands in pockets; john mellencamp greatest hits
John Mellencamp (1983)Mark and Colleen Hayward / Contributor / Getty

His life and career have taken some some dramatic turns themselves, from his childhood struggles with spina bifida to a 1994 heart attack, and his determination to break free from the Johnny Cougar name and persona he was forced to take on by record label suits early on in his rise to fame. “I really hated [that name] for a long time. Now I’m kind of happy about it,” he told Esquire. “It made me work twice as hard as I probably would have. It’s like that Johnny Cash song ‘A Boy Named Sue.’”

And work hard he did — even if the hitmaker and lifelong painter is somewhat critical of some of his earlier efforts. “If you listened to some of my first albums, you’d ask: Why did you even continue? My first records are that bad. My first paintings are that bad. Terrible. But I kept going.” To date, he’s released 24 original albums in his 48-year career, the most recent being 2023’s Orpheus Descending.

man clapping
John Mellencamp (2023)Gary Miller / Contributor / Getty

The musician is thankfully still going strong — and he doesn’t plan on calling it quits just yet. “I’m 72, and I’m still doing a teenager’s job,” he told the Washington Post, noting that he’s aware some of his heroes and contemporaries are no longer around. “I’ll be working out [these days] with an iPod and a song will come on and I’ll go, ‘Well, that [expletive] guy’s dead. This guy’s dead. What happened to this guy?’” His goal, he told Esquire a couple of years ago, “is to get to 80. That gives me 10 years. Do you know how fast 10 years goes by for me? I’ve got only 10 summers left. Ten summers is not that long.”

That’s why it’s important for him to make the most of the time he still has, both onstage and off. Mellencamp, a father of five, has three daughters and two sons ranging in age from 29 to 53. “I don’t know how many grandkids I have. A lot,” he quipped to Esquire, but they all bring him great joy. “I’ve never cared about my image — just about my family, my kids,” the musician told People.

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man at podium
John Mellencamp at 23rd Annual Rock and Roll Hall of Fame Induction Ceremony (2008)Dimitrios Kambouris / Staff / Getty

And the artist — who was inducted into the Rock & Roll Hall of Fame in 2008 — cares about his fans, many of whom got to see him play on his Live And In Person Tour that wrapped up in April. Next up for the rocker are dates from July through September on the Outlaw Music Festival, on which he’ll join other great artists such as Willie Nelson, Bob Dylan, Brittney Spencer, and Robert Plant and Alison Krauss.

While you keep an eye out for those festival appearances, let’s take a look — and a listen! — to John Mellencamp’s greatest hits from his six-decade career.

15. “Pop Singer” (1989): John Mellencamp greatest hits

“Never wanted to be no pop singer. Never wanted to write no pop songs.” This tune coyly thumbs its nose at anyone who underestimated the artist’s work early in his career. “Any time anybody would want to diminish what I might have accomplished, they would refer to me as a pop singer,” Mellencamp explained to Billboard in 2001. “In reality, my songs were rock-folk songs that were on pop radio.”

14. “Hand to Hold On To” (1982)

“Don’t need to be no strong hand. Don’t need to be no rich hand. Everyone just needs a hand to hold on to.” When the young and not-yet-successful artist gave this tune, along with a few others, to his rep at the record label, “He hated them. Hated them! He said, ‘We expect you to become the next Neil Diamond. What is this sh—?,’” Mellencamp recalled to Rolling Stone. Luckily, he persevered and fans went on to truly love this reassuring and relatable track.

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13. “Rain on the Scarecrow” (1986): John Mellencamp greatest hits

“Rain on the scarecrow, blood on the plow. This land fed a nation, this land made me proud.” Mellencamp tackles how 80s politics and the economy took a toll on farmers all across the nation in this powerful anthem. “Our songs always came about the same way: talk around the kitchen table,” he told Rolling Stone. We did our research and wrote this song.… Talking to people was heartbreaking. Nobody wanted to lose their farm.”

12. “Cherry Bomb” (1987)

“Laughin’, laughin’ with our friends. Holdin’ hands meant somethin’, baby.” This nostalgic and catchy charmer topped the Billboard Mainstream Rock charts as it transported us all to the club Cherry Bomb, yeah yeah yeah… Four other vocalists are featured on this track, which was inspired by Sly and the Family Stone. “He had all those hit records when I was in junior high, and I love the fact that all the sudden there’s a female voice, then a male voice,” Mellencamp once told GQ.

11. “Wild Night” (1994): John Mellencamp greatest hits

“And the people passing by just stare with wild wonder, and the inside jukebox roars just like thunder.” Singer Meshell Ndegeocello joined Mellencamp on this awesome and energetic Van Morrison cover that got listeners to come on out and dance in the 90s. “I went to Indiana,” Ndegeocello told Songfacts of working with the rocker. “He took me back to my roots where you just have a band in the studio and you played together. There was no clique. It was just trying to create a vibe and humanity. He was really nice to me. That’s one of the great experiences of my life.”

10. “Check It Out” (1988)

“Getting too drunk on Saturdays (Check it out). Playing football with the kids on Sundays

(Check it out).” This is a crowd favorite that gets the audience singing along at most Mellencamp concerts. Its comforting and danceable groove even cushions some of the lyrics that detail the drudgery and struggles of middle-class life (going back to work on Monday, paying the utility bills, etc.). 

9. “Paper in Fire” (1987): John Mellencamp greatest hits

“Who’s to say the way a man should spend his days? Do you let them smolder like paper in fire?” The artist told his biographer Paul Rees that this tune was influenced by the generations of men who came before him in the Mellencamp family, such as his Uncle Joe, who “never bought his wife a birthday or Christmas present [and] never even told her he loved her… [yet my] Aunt Rose was so devoted to this guy she would’ve set herself on fire for him.”

8. “Key West Intermezzo (I Saw You First)” (1996)

“She stirs the ice in her glass with her elegant finger. I want to be what she’s drinking, yeah I just want to be…” This peppy, flirty tune fittingly was the lead-off single from Mellencamp’s Mr. Happy Go Lucky album. It proved to be his last Top 40 hit, reaching No. 14 on the Billboard Hot 100, though it went all the way to No. 1 on the Adult Alternative chart. The song “felt natural,” music journalist John Barber wrote on Analogue about the song’s sound and direction. “There wasn’t selling out here, there was simply growing up. And man, it was cool.”

7. “Lonely Ol’ Night” (1985): John Mellencamp greatest hits

“It’s a lonely ol’ night. Can I put my arms around you?” Mellencamp named one of his sons, Hud, after the Paul Newman movie this song was inspired by. “What I learned from [Bruce Springsteen’s songwriting] was to be a good observer of life. You don’t have to be the person. You can watch,” Mellencamp told Central Indiana’s WTHR about this winning tune, which they called “a thematic cousin to Springsteen’s 1984 hit ‘Dancing in the Dark’ in the narrators’ late-night search for a connection.”

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6. “The Authority Song” (1984)

“Well, I been doing it since I was a young kid and I’ve come out grinnin’. Well, I fight authority, authority always wins.” This is classic Mellencamp, flexing his defiant muscles throughout. He once told Creem magazine that it was “our new version of ‘I Fought The Law’” by The Crickets, which was later done by The Bobby Fuller Four and The Clash. In its accompanying video, Mellencamp fittingly performs the song inside of a boxing ring.

5. “Hurts So Good” (1982): John Mellencamp greatest hits

“Come on baby, make it hurt so good. Sometimes love don’t feel like it should.”  Though he’d later note this tune is ultimately about “juvenile topics,” Mellencamp didn’t feel bad about hitting it big with this No. 2 song, which won him a Grammy for Best Rock Vocal Performance, Male — his only win at those awards out of the 14 nominations he’s earned throughout his career.

4. “Crumblin’ Down” (1983)

“Saw my picture in the paper, read the news around my face. And now some people don’t want to treat me the same.” This Top 10 hit touches upon how people’s perceptions of Mellencamp, and even how he viewed himself, changed after his breakout success. “I turned into the guy I hated — the guy who’s on the radio all the time and…dealing more with business sometimes than music,” he explained to Creem. “I think writing [this song] helped me. Because when the walls come crumblin’ down — when all the big-time deals fall through — I’m still going to be the same old trouble you’ve been having for years.”

3. “Pink Houses” (1983): John Mellencamp greatest hits

“Ain’t that America? Home of the free, yeah. Little pink houses for you and me.” This was a red-hot hit for Mellencamp, and one with a veiled, biting message. “This one has been misconstrued over the years because of the chorus — it sounds very rah-rah,” the artist explained to Rolling Stone, “But…the American dream had pretty much proven itself as not working anymore. It was another way for me to sneak something in.”

2. “Small Town” (1985)

“Well, I was born in a small town. And I can breathe in a small town. Gonna die in a small town. Oh, and that’s probably where they’ll bury me.” Mellencamp has noted that this popular anthem of his is “a song that felt as though Woody Guthrie had sent it to me from the grave.” He told the Washington Post that when he played the future No. 6 track, “a valentine to his hometown of Seymour, Ind.,” for his wife at the time and his Aunt Tootes, “they went dead quiet. When you play what you’ve done for a family member and you get that kind of reaction, you know you have something.”

1. “Jack & Diane” (1982): John Mellencamp greatest hits

“Changes come around real soon, make us women and men.” This No. 1 smash helped put Mellencamp on the musical map and it’s stood the test of time — and it’s even grown on the songwriter throughout the years. “In the eighties and nineties, I hated singing the line ‘Life goes on, long after the thrill of livin’ is gone.’ Now I love it,” Mellencamp told Esquire, adding to Rolling Stone, “I think people, particularly in the Midwest, really identified with these characters. I can’t tell you how many people have come up to me and said, ‘I’m Jack and I’m Diane. You wrote about my life.’ To me, that’s a successful song.”

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