I went on a long, very long, very very long, 5000-mile road trip recently with my family. It was fun, and I would not recommend it to anyone.

My wife got the idea to make a Spotify playlist for the road to teach our kids about popular music. So together, we compiled a list of songs and artists that we regarded as historically and artistically significant. We didn't really approach it in any kind of scholarly way, just stuff off the top of our heads, but still, it grew to 150 songs pretty quickly. A second list of other songs we had forgotten was nearly as long. I stand by almost all of our choices (not sure Iron Maiden's "Flight of Icarus" needed to be there) and if I have any issue with the lists, it's that they omitted way, way too many songs. Hugely significant artists were left off, entire genres were ignored, groundbreaking albums were absent. We spaced on Elton John, neglected early MTV pop.

It got me thinking about how this would have been done in the 1980s. That's right: mix tape. Cassette. Maybe 20 songs tops on a 90-minute tape. Twenty songs I would need to select that explain the entirety of popular music over the last, say, half-century. Impossible. THEN, I wondered if it could be reduced even further. Five songs.

Okay, so thought exercise.

Let's say a space alien comes to Earth and vows to blow the planet up UNLESS we provide a thorough understanding of the last 50 years of popular music. Thing is, the alien only has time to listen to five songs. Aliens are busy. The alien wants rock, pop and rap to be on the list, but doesn't want any country, jazz or classical. And no showtunes. The alien was very clear about no showtunes.

So with THE WORLD AT STAKE, what five songs do you choose?

For me, the process meant accepting certain things:

• Anyone's list is going to be colored by his or her own experiences and tastes. I never got into Southern rock or boy bands, for instance, and don't know those genres that well, so therefore can't judge them.

• Is history better explained by the influencer or by those influenced? Michael Jackson or Bruno Mars? Madonna or Britney or Ariana Grande? Do you pick one side or try to do it all?

• This is an impossible assignment and our planet will get blown up.

• A song can be one of the greatest of all time but still not make the list if it didn't serve to explain the rest of music. Sure, "Bohemian Rhapsody" is fantastic but it is anomalous. It didn't spur a movement because no one is Freddie Mercury.

Anyway, it's a good mental exercise when you're trying to stay awake whilst driving across Wyoming.

I do have my list. You will disagree with it. But first, songs that didn't quite make the final five:

Satisfaction - The Rolling Stones — It is the embodiment of teen angst and has a brassy guitar riff, both crucial to rock n' roll. It also has that heavy American blues footprint of early Stones. In the end, I had to go with other songs that could cover even more than that.

99 Problems - Jay-Z — A well-crafted execution of hip-hop, but I don't think it illuminates what came before or after it.

Thriller - Michael Jackson — My list contains no MJ. No high-pitched male pop vocal with loads of dance moves at all. Sorry, JT. Apologies, Mr. Mars.

Doll Parts - Hole — A surprisingly strong run for Ms. Love and company with a song that covered punk, grunge, deconstruction of female archetype, and more.

Blitzkrieg Bop - Ramones — Manages to cover early punk while also nodding to simple verse-chorus-verse arrangements and even nodding to surf music. One of the last cuts.

London Calling - The Clash — Punk without crass commercialism, melding the form into rock and influencing everyone with a guitar. But also a great deal about flooding.

God Only Knows - The Beach Boys — Here's another band that ended up doing something beautiful and amazing while not really creating a huge trend. Few theremins appeared after them.

Hotel California - Eagles — Gives us the California sound with a laid-back groove and harmonies. Also offers themes about drugs and epic storytelling. Is a bad song but that doesn't disqualify it. Simply no room.

Iron Man - Black Sabbath — Covers both the heavy metal genre and protest music. What? Yes! It's about someone traveling back from the future to warn us of the apocalypse and to change our ways.

Respect - Aretha Franklin — Leaving this off kills me to death. I opted for a different powerful female singer instead but I hate myself so much for not putting this on.

Born to Run - Bruce Springsteen — In many ways, a perfect rock song. Here's what you get over the course of four minutes and thirty-one seconds: sweat, American dream, cars, highways, hating your hometown, sex told through the most unsubtle metaphors ever, Clarence Clemons' saxophone, a glockenspiel(!), and death.

Also considered:
The Weight - The Band
Changes - David Bowie
Goodbye Yellow Brick Road - Elton John
We Got The Beat - The Go-Go's
Purple Rain - Prince
Tangled Up In Blue - Bob Dylan
Toxic - Britney Spears
One - U2 and/or Johnny Cash
California Love - 2pac feat. Dr. Dre
Hey Ya! - Outkast
…and a million others.

In the end, I relied on five songs that gave me versatility and that covered a lot of ground in the space of one track. Not the best songs, mind you, but the most instructive. Here they are in order of release date.

Lucy In The Sky With Diamonds - The Beatles — In this track from maybe the band's best album, 1967's Sgt. Pepper's Lonely Hearts Club Band, you have so many ingredients. The lyrical imagery and trippy sitar point to psychedelia and, by extension, drugs. You also have such perfect pop hooks, the kind generations of songwriters have aspired to. I'd even argue you get some hints of prog-rock to come bursting through on this and many other songs on one of the first mainstream concept albums. Really, you could take many of the tracks off Sgt. Pepper's and put it on this list.

What's Going On - Marvin Gaye — Gaye's 1971 classic regularly appears on very short lists of the best songs ever and deservedly so. It's art that takes on the heavy burden of a turbulent time and was inspired by incidents of police brutality as well as the Watts riots. At the same time, it insists on hopefulness, demands we "find a way to bring some loving here today", and insists that only by talking to each other can we see what's going on. To the alien in our organizing concept, it brings social consciousness, soul and soul music, and one of the great voices of all time. Plus the phrase, "Right on, right on."

Take On Me - A-ha — Look. In order to save the world, we have to do as the alien instructed. And it wasn't to make a set of great songs. This 1985 number isn't a great song or even a good song. Or even a song I can actually stand to listen to. But it explains so much because it is pure artifice. Bland lyrics that hint at bland love or are perhaps words that sound okay together. You have a synthesizer that basically punches you in the ears over and over, AS SO MANY OTHER SYNTHESIZERS HAVE. You have an immediate mental image of that bizarre race car driving MTV video. You have a generically good-looking singer. There is a great deal of music in our time that is this vapid and while I'd love to get the alien to listen to more Leonard Cohen and Laura Nyro, this is more honest. I'm sorry.

Smells Like Teen Spirit - Nirvana — This 1991 song sneers. It sneers in the lyrics ("Here we are now, entertain us, I feel stupid and contagious"), it sneers at the very upbeat pop riff it's built around, and it's all presented by a guy who sneered at the world. Even the title is a sneer: words that don't appear in the song and that reference a deodorant and some Kathleen Hanna graffiti. We don't have prototypical punk bands on our list of five so Kurt's sneers will have to do. Plus, including it lets us take a nod to the Pixies, whose sound it's modeled on.

Crazy in Love - Beyoncé feat. Jay-Z — By now, we should all know that we are lesser beings to Beyoncé and that we are merely fortunate to live in a world at the same time as her. Even before the Lemonade album, she was the culmination of a ton of different and disparate musical forces that came before her from pop to soul, from Aretha to Madonna and it's on full display in this 2003 track. THEN you add in one of the most successful rappers and music moguls in history to teach the alien about rap, business, and self-referentialism. Together, they make a love song that's a more powerful earworm than any our planet has to offer.

Yeah, yeah, I know: "How dare you, you're way off, you don't know music at all, you got the planet blown up."

So what do YOU think? What songs would you choose? Share your lists below.