1. “Monday, Monday” by The Mamas & The Papas
This 1966 hit was everywhere at the time, even winning a Grammy for Best Pop Performance. Its dreamy harmonies and bittersweet lyrics captured the mood of the mid-’60s perfectly. The Mamas & The Papas were known for blending folk and pop, and “Monday, Monday” felt like their crowning achievement. For a while, it was the soundtrack of a generation.
But despite its big impact, you don’t hear it much now. Stations lean more toward “California Dreamin’” when they want to play this group. That doesn’t change the fact that “Monday, Monday” was a chart-topping sensation. It’s a song worth revisiting when you want to remember just how influential harmony-driven pop once was.
2. “Kind of a Drag” by The Buckinghams
When this song hit number one in early 1967, it was a surprise smash. The Buckinghams blended horns with rock rhythms, creating a distinctive sound that was a step ahead of its time. “Kind of a Drag” was catchy, slightly melancholy, and instantly memorable. It gave the Chicago band their biggest moment.
Yet today, the song doesn’t pop up often, even on oldies playlists. Their style was overshadowed by bigger acts like Chicago and Blood, Sweat & Tears. Still, in its moment, “Kind of a Drag” was the epitome of cool. It’s one of those forgotten gems that once ruled the radio.
3. “Windy” by The Association
In 1967, “Windy” was absolutely unstoppable. With its upbeat lyrics and lush harmonies, it quickly soared to number one and stayed there for weeks. The Association had a knack for earworms, and this song was their brightest, breeziest hit. People couldn’t help but hum along.
Now, though, it’s rarely played. Radio stations usually lean on “Cherish” when they want an Association tune. But “Windy” is pure ’60s joy, the kind of song that instantly puts you in a good mood. It deserves a little more love today.
4. “Last Train to Clarksville” by The Monkees
The Monkees were TV-made stars who proved they could deliver hits just as catchy as their contemporaries. “Last Train to Clarksville,” released in 1966, was their first big single, and it raced to number one. With its jangly guitars and train-like rhythm, it felt both fun and slightly mysterious. Fans adored it.
But outside of Monkees fan circles, it doesn’t get much play now. Instead, people remember “I’m a Believer” or “Daydream Believer.” Still, “Last Train to Clarksville” was the song that proved the group had real staying power. It was the first stop on their pop takeover.
5. “She’d Rather Be With Me” by The Turtles
The Turtles had one of the biggest songs of the decade with “Happy Together,” but “She’d Rather Be With Me” was another smash. Released in 1967, it was playful, upbeat, and just as catchy. It hit the top ten and cemented the band as a major player in the pop scene.
These days, though, it’s mostly forgotten in favor of their biggest hit. That’s a shame, because it has the same charm and energy. When you hear it, it feels like summer bottled into a song. The Turtles knew how to make happiness sound effortless.
6. “Baby I Need Your Loving” by The Four Tops
The Four Tops were Motown legends, and this was their first big hit back in 1964. With Levi Stubbs’ powerful voice leading the way, it was soulful, heartfelt, and instantly recognizable. It became a cornerstone of Motown’s rise in the ’60s.
And yet, it doesn’t get the same rotation as songs like “Reach Out I’ll Be There.” Modern playlists tend to skip over it, even though it’s one of their strongest tracks. Hearing it today is like a reminder of just how good Motown’s early years were. It’s pure soul perfection.
7. “A World Without Love” by Peter & Gordon
Written by Paul McCartney, this song became a number one hit in 1964. The British duo delivered it with sweetness and sincerity, and fans around the world swooned. It was part of the British Invasion wave that introduced new sounds to American audiences.
But it doesn’t pop up much anymore, even in Beatles-related playlists. That’s surprising, given its chart success and connection to McCartney. It’s a reminder that the ’60s produced so many hits, some simply slipped through the cracks. This one deserves another spin.
8. “I’m Henry VIII, I Am” by Herman’s Hermits
In 1965, Herman’s Hermits took this old music hall song and turned it into a pop sensation. It was silly, repetitive, and completely unforgettable. Fans loved its humor, and it gave the band one of their biggest U.S. hits.
These days, though, it’s largely forgotten. Other Herman’s Hermits tracks like “I’m Into Something Good” tend to stick around more. Still, “I’m Henry VIII, I Am” was a defining moment in their career. It’s proof that sometimes, a goofy little tune can climb all the way to the top.
9. “Love Can Make You Happy” by Mercy
This tender ballad became a huge hit in 1969, soaring into the top five. Its soft melody and gentle lyrics made it a wedding and prom favorite. For a time, Mercy looked like they were set to be the next big thing.
But like many one-hit wonders, the group faded fast. Today, you hardly ever hear it, even though it was once inescapable. Still, its sweetness holds up beautifully. It’s one of those lost slow-dance songs that instantly transports you back.
10. “Love Is All Around” by The Troggs
The Troggs are most famous for “Wild Thing,” but “Love Is All Around” was their softer side. Released in 1967, it was heartfelt and romantic, showing that the band could do more than garage rock. It became a top ten hit and a favorite for couples.
Nowadays, though, most people remember the ’90s cover version instead. The original doesn’t get the attention it deserves. It’s a reminder of just how versatile The Troggs really were. A little rough around the edges, but full of heart.
11. “Lady Willpower” by Gary Puckett & The Union Gap
Gary Puckett’s booming voice defined several hits in the late ’60s, and “Lady Willpower” was one of the biggest. Released in 1968, it blended pop with drama in a way that felt larger than life. Fans adored his commanding delivery and theatrical style.
But over time, songs like this slipped into the background. Today, you rarely hear it compared to other late ’60s hits. That doesn’t mean it’s lost its power, though. Puckett’s voice still makes it unforgettable once you press play.
12. “This Diamond Ring” by Gary Lewis & The Playboys
In 1965, this song was a monster hit, climbing all the way to number one. Gary Lewis, the son of comedian Jerry Lewis, fronted the Playboys and became a teen idol almost overnight. The jangly pop tune was irresistible to fans, with its mix of heartbreak and energy. It seemed like Gary Lewis was destined for long-term stardom.
But like many teen idols of the decade, his fame burned hot and fast. “This Diamond Ring” doesn’t get much radio play today, overshadowed by other hits of the British Invasion era. Still, for those who remember, it’s one of those songs that defined the mid-’60s pop sound. It’s a track that deserves a comeback.
13. “Sheila” by Tommy Roe
Tommy Roe was sometimes called the “bubblegum king,” and “Sheila” was the song that put him on the map in 1962. Its simple, rockabilly-inspired beat and catchy chorus made it an instant classic. Fans loved its mix of innocence and energy, and it shot to number one on the charts. Roe quickly became one of the decade’s most recognizable voices.
Yet you almost never hear “Sheila” today, even though it was such a big deal at the time. Later hits like “Dizzy” tend to get more attention, leaving this one in the shadows. But if you give it another listen, you’ll hear why it connected so strongly. It’s pure early-’60s charm wrapped in two and a half minutes.
14. “Bus Stop” by The Hollies
The Hollies were one of the most reliable hit-makers of the ’60s, and “Bus Stop” was one of their best. Released in 1966, it told the story of a romance that blossomed while waiting for the bus in the rain. With its jangly guitars and tight harmonies, it became a top ten hit in both the U.S. and the U.K. Fans couldn’t get enough of its catchy chorus.
Still, despite the Hollies’ influence, “Bus Stop” isn’t heard much anymore. Stations tend to lean on their later hits like “Long Cool Woman in a Black Dress.” But “Bus Stop” was a defining moment in their career and a song that deserves more airtime. It’s one of those tracks that perfectly captures the pop brilliance of the mid-’60s.
