Mind the (Age) Gap: Top 20 Cradle-Robbing & Cougar Anthems

04 Sep

Have you ever watched one of those “Awesomely Bad” countdowns on VH1? You know how you get sucked in, and they get to a song that you absolutely loved growing up? Yeah? Then you suddenly realize why it’s “awesomely bad”. Seriously, we let a lot of artists and musicians get away with some questionable and downright bad lyrics. That brings me to this playlist. After putting my iPod on shuffle a million times, I have realized that there are tons of songs by and/or about cradle robbers. If you don’t know what that term means, allow me to explain. It refers to a person who dates, sleeps with, and/or lusts after someone significantly younger. As usual, I spent a lot of time researching songs because I love doing these kinds of lists (Cheater Playlist, Father to Son, Seductive Serenade). Honestly, some of these songs just made me feel gross. There are some that have blatant disregard when it comes to…carnal interaction with an underage party. From my research, I found that the 70’s and 80’s as decades were repeat offenders. A few of these songs require a bit of reading between the lines and are open for interpretation, but this is my list. For the most part, I have elected to stay away from awesomely bad obnoxiously horrible and illegal songs (I’m looking at you, KISS, Motley Crue, and ZZ Top). With that said, I present my Top 20 Cradle-Robbing & Cougar Anthems.

Disclaimer (why do I keep having to write these?): I do not condone, support, and/or encourage statutory rape. Thank you.

20. “Stray Cat Blues” – The Rolling Stones (1968)
I tried really hard to avoid these overtly statutory songs, but the Rolling Stones had absolutely no shame, so I picked this song to lead off. These days, people love Sir Mick Jagger. Hell, there are songs about him setting the bar for swagger levels. However, when The Rolling Stones were at their height, this musical enabler of pedophiles was born.
Why it’s on the list: “I can see that you’re 15 years old / No I don’t want your I.D.”

19. “Tonight I’m Gonna Rock You Tonight” – Spinal Tap (1974)
The Department of Redundancy Department called me earlier and told me about this one. Like the song before, I really tried to avoid it. Here’s your typical rock song about being on tour and sleeping with a groupie who got backstage passes. The problem is that she’s underage. Way underage. Ugh…
Why it’s on the list: “You’re sweet, but you’re just four feet / And you still got your baby teeth / You’re too young, and I’m too well hung”

18. “Jennifer” – Styx (1976)
The infamous age of 17 makes its first appearance here. Thankfully, Styx isn’t as disgustingly bad as the Rolling Stones and Spinal Tap were. Interestingly enough, the young lady described in this song seems to be the aggressor.
Why it’s on the list: “She’s 17, barely old enough to cry / A child in her father’s eyes /
A woman every night”

17. “Young Man, Older Woman” – Millie Jackson (1991)
Ah, yes. We finally get to hear from the women. And Millie Jackson at that. If you aren’t familiar with Ms. Jackson, she’s notorious for her authentic, brash, scandalous, highly sexual, and brilliant musical storytelling. This track doesn’t stray from that formula. Like the song (and play/album) title says, this is a tale about a cougar before cougardom was cool. There’s no sign of illegal activity here. Thank God.
Why it’s on the list: “You gotta be crazy / You’re much too young / Or haven’t you noticed? / You could be my son”

16. “Father Figure” – George Michael (1988)
As I said before, this list involves some interpretation. Although George Michael never reveals ages in this song, I’m of the opinion that he’s singing about something against the law here. Michael croons about “tiny hands”, being “naked”, and “crime”. As far as I’m concerned, George was robbing the cradle and pulled the wool over our eyes (ears). I hate that I like this song.
Why it’s on the list: “I will be your father figure / Put your tiny hand in mine / I will be your preacher, teacher / Anything you have in mind / I will be your father figure / I have had enough of crime”

15. “That Summer” – Garth Brooks (1993)
Switching gears, but remaining in overdrive, Garth Brooks supplied this gem. I knew I could count on country to give me something good. Honestly, I think this is lyrically one of the best songs you’ll find on this countdown. Brooks mastered the art of storytelling and paints a vibrant picture of losing his virginity to an older woman in a wheat field in the middle of nowhere during that summer. Hooray for prepositional phrases.
Why it’s on the list: “I went to work for her that summer / A teenage kid so far from home / She was a lonely widow woman / Hell bent to make it on her own”

14. “Desiree” – Neil Diamond (1977)
Rule of thumb: a song with a female’s name as the title is very hard to forget…for better or for worse. Off the top of my head, there’s “Jennifer”, “Amanda”, “Kisha”, “Iesha”…and “Desiree”. Much like Garth Brooks’ tale, Neil Diamond sings of losing his virginity to a woman twice his age during the summer. Anybody else noticing a serious difference in tone when the song is about a younger guy and an older woman?
Why it’s on the list: “On that younger day / Well, I became a man / At the hands of a girl / Almost twice my age”

13. “Fat Bottomed Girls” – Queen (1978)
See: “That Summer” and “Desiree”. Queen broke the mold slightly by resorting to the older women because the women comparable in age just didn’t seem to be doing it for them anymore. Keeping with the theme, these “fat-bottomed girls” forever changed the way these young men looked at life.
Why it’s on the list: “Hey, I was just a skinny lad, never knew no good from bad / But I knew life before I left my nursery / Left alone with big, fat fannies, she was such a naughty nanny / Heap big woman you made a bad boy out of me”

12. “Seventeen” – Winger (1988)
Is it just me or were there a lot of songs about big age differences coming out during the 80’s? Here, we have another 17-year-old female aggressor. At least, that’s the way the story is told. I’m not sure how old the guys are in this song, but they equate sex to love. They must be pretty young. I still smell a statutory situation.
Why it’s on the list: “I’m only 17, but I’ll show you love like you’ve never seen / She’s only 17, daddy says she’s too young, but she’s old enough for me”

11. “Don’t Stand So Close to Me” – The Police (1980)
The Police knew how to say…wait for it…no! I can’t stress how happy I am to put this song here. Sting tells us about a young teacher (it happens to be him during his teaching days) that some of the school girls have a crush on. People are speculating that something is going on with this teacher and one of his pupils. However, he turns down the student’s advances and tells her not to stand so close. Good for you, Police, for staying on the right side of the law.
Why it’s on the list: “Inside her there’s longing / This girl’s an open page / Book marking, she’s so close now / This girl is half his age”

10. “Hot For Teacher” – Van Halen (1984)
Staying in the classroom, but flipping the script, Van Halen is responsible for this classic. Yep, it’s the 80’s again. These headbangers gave us an album called “For Unlawful Carnal Knowledge”, so it’s no surprise that they landed in the middle of this infamous collection of hit songs. I can tell you there are plenty of guys who have or have had a crush on one of their teachers. Guilty. Van Halen just made this coming-of-age milestone into a song. Somewhere Mary Kay Letourneau is listening to this song on her iPod.
Why it’s on the list: “I got it bad, so bad / I’m hot for teacher”

9. “Just Can’t Handle It” – Hi-Five (1990)
File this song away under the category of songs I sang as a young buck not fully understanding its true meaning. I respect the vulnerability expressed on this track, though. Instead of a pompous and cocky attitude that one would expect from a teenager close to his sexual peak, “Just Can’t Handle It” reveals a 16-year-old who knows he’s not ready for a 25-year-old.
Why it’s on the list: “Cutie tried to flip me; tried to blow my mind / I was only 16; she was 25”

8. “Age Ain’t Nothing But A Number” – Aaliyah (1994)
While none of R. Kelly’s songs made it to this playlist (I tried really hard to find one), this comes close enough. Kelly wrote and produced this one. Oh, yeah, he also scandalously (and illegally) eloped with Aaliyah when she was 15. He was 27. That’s neither here nor there, though. “Age Ain’t Nothing But A Number” is a smooth track from the beautiful songbird, Aaliyah, about a young girl wanting to date an older man. Slick.
Why it’s on the list: “Age ain’t nothing but a number, throwing down ain’t nothing but a thang / This loving I have for you it’ll never change”

7. “Stacy’s Mom” – Fountains of Wayne (2003)
In the same vein as “Hot for Teacher”, there is this ode to teenaged, male ardency. While not as serious as most of the other songs, “Stacy’s Mom” is a strangely loveable song about a guy interested in someone’s mother. What gives this song its high ranking is the fact that the mother the singer wants is his girlfriend’s. Cold-blooded.
Why it’s on the list: “You know I’m not the little boy that I used to be / I’m all grown up now, baby, can’t you see?

6. “Love You Down” – Ready For the World (1986)
Who knew that the confidence and (legal) swagger that this list was missing would be supplied by an R&B slow jam? Once again, we meet a young, male lover who aims to please his woman. Her friends aren’t a big fan of their relationship because of the age gap, but he boldly reminds everyone that he’s a smooth operator who will do whatever it takes to please his girlfriend…even if it takes all night.
Why it’s on the list: “All your friends think I’m just too young for you / You tell ’em that I can do what guys their age can’t do, oh, baby”

5. “Mrs. Robinson” – Simon & Garfunkel (1968)
Okay, okay, okay…I caved. This song makes no mention of an age gap, but it’s probably one of the first songs that comes to mind when you think of MILF/cougar anthems thanks to The Graduate.
Why it’s on the list: Mrs. Robinson (Anne Bancroft) has an affair with the younger Benjamin Braddock (Dustin Hoffman) in The Graduate. The rest is history…

4. “Maggie May” – Rod Stewart (1971)
And here’s what can happen when a younger man gets intimate with an older, seasoned woman. Rod Stewart falls for the woman who stole his heart, and she ended up making a fool out of him. She wanted physical, and he got emotional. It happens.
Why it’s on the list: “The morning sun, when it’s in your face / Really shows your age / But that don’t worry me none / In my eyes, you’re everything”

3. “Let’s Get It On” – Marvin Gaye (1973)
I’d like to think that I’m good for a surprise or two when it comes to these playlists. “Let’s Get It On” is that surprise. Let me explain. Yes, I get that you sing along with this when you hear it on commercials, during the old-school lunch breaks, and at grown & sexy social scenes, but Marvin was up to no good when he wrote it. When he recorded it, he was dating Janis Hunter, the daughter of jazz guitarist, Slim Gaillard. The problem is that Janis was…you guessed it, 17. Marvin was literally twice her age. The two eventually married, had two children, and got divorced. That puts a different spin on this number, doesn’t it?
Why it’s on the list: “There’s nothing wrong with me / Loving you, baby, no, no / And giving yourself to me can never be wrong / If the love is true”

2. “Into the Night” – Benny Mardones (1980)
How did this song become a hit? Why did this song become a hit? Why do I find myself singing this song in the car? You don’t even have to listen closely to know what it’s about. The first lines of the song tell you that Benny is in love with a 16-year-old, and other people (rightfully) do not approve. What’s a man to do? Take said 16-year-old into the night, and show her a love like she’s never seen. Someone get Chris Hansen on the line!
Why it’s on the list: “She’s just 16 years old / Leave her alone / They said…”

1. “Wrapped Around Your Finger” – The Police (1983)
For those of you keeping score at home, there have been six songs from the 70’s and six songs from the 80’s on this list. Well, the 80’s called…again…to break the tie. The Police are no strangers here (see: #11), but this song is king in my mind. Sting is one hell of a songwriter. With that talent, comes a complicated tale that essentially has two different interpretations. “Wrapped Around Your Finger” would make an English professor proud with all of the literary allusions and inferences. My interpretation: Sting takes on the persona of a curious, young paramour who is wrapped around the finger of an older woman who happens to be married. Eventually, Sting gets hip to the game that his lover is playing and turns the tables on her. Instead of him being wrapped around her finger, she becomes wrapped around his…presumably because of the physical aspect of their affair.
Why it’s on the list: “You consider me the young apprentice / Caught between the Scylla and Charibdes / Hypnotized by you if I should linger / Staring at the ring around your finger”

That does it for me. There are songs from the 2000’s, 90’s, 80’s, 70’s, and 60’s that span across a myriad of genres. This age gap thing has been going on since the beginning of time. Unfortunately, musically, it is grossly over-saturated by male singers/groups. Ugh…I need to take a shower because some of these songs make me feel grimy. Did I leave something off? Let me know your thoughts.



Posted by on September 4, 2012 in Countdown, Music, Relationships, Sex


12 responses to “Mind the (Age) Gap: Top 20 Cradle-Robbing & Cougar Anthems

  1. Tanna

    July 7, 2013 at 8:10 PM

    Years ago age gaps weren’t seen as a huge deal. There was a time that 10yr age gaps were the norm. Your ladies mature faster than boys their age and are natually attracted to men a bit older. How much older depends on the young lady.

    Admittedly a lot of music over many generations is not the best moral compasses for sure.

    • realist23

      July 7, 2013 at 8:29 PM

      I don’t see them as a bad thing. I’ve dated quite a few women older than I am. I had fun putting this list together, though.

  2. Mike

    September 17, 2013 at 8:12 PM

    Ummm… Edge of Seventeen, by Stevie Nicks? The ultimate Cougar anthem.

    • realist23

      September 18, 2013 at 9:04 AM

      That was one of the first songs I thought would be on this list, but the more I listened to it and the more I researched it, I realized that it’s not a cougar anthem. It’s really about death. Nicks wrote it after John Lennon and her uncle died. There are some lines, however, that could be interpreted as cougarish.

    • diane

      July 17, 2015 at 6:58 PM

      Got to be my fave cougar anthem, a though he’s 21 not 17. I’m still a good few years older than him lol

  3. raeynah

    March 22, 2014 at 10:51 AM

    Maggie May by Rod Stewart.

  4. Lol

    March 24, 2014 at 4:50 PM

    The INOJ remake of “Love You Down”. The genders are flipped, and it’s a dance song.

  5. mattbarnard43

    April 23, 2015 at 7:21 PM

    I was listening to Styx’s “Jennifer” tonight and got thinking, “Dang… what were they thinking? Dennis DeYoung was definitely in his mid-20s when he was writing about this 17 year old girl who was, quote, a woman every night.” I figured someone out there had to be catching onto the same thing. I plugged in three terms to Google: “Styx”, “Jennifer” and “Statutory”. Voila!

    • faemac123

      June 21, 2016 at 1:42 PM

      yeah some songs are pretty bad, but personally im 15 and am dating a 21 year old. so i cant judge that.

  6. mwalimu

    October 4, 2016 at 4:06 PM

    One that I’m surprised hasn’t turned up on any of these ‘cougar song’ lists is “Summer (The First Time)”, a 1973 midchart hit by Bobby Goldsboro.

    • realist23

      April 6, 2017 at 2:17 PM

      That’s a great one. It definitely should’ve made the list.


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