A friend was at a family reunion. The group he was in (made up mostly of people in their early 60’s) was talking about the Beatles. Someone’s 15 year old kid was listening in to the conversation and at one point said that he had heard of the Beatles, but never really listened to any of their songs. Some in the group suggested that he listen to certain songs to get an idea of what the Beatles’ music was like.
What songs would you have suggested?
Isn’t “Yesterday” still top of their chart? Mighty hard to beat, anyway.
Easy: either the Red collection album, or one of the first two middle period albums, Help or Rubber Soul. You’re done; the music will pull him in if he wants it to.
The “One” album is a nice selection of their hits across the years. Covers their basic trajectory reasonably well, though it skips over the weirder stuff from the Magical Mystery Tour and White Album years.
My first Beatles album was Rubber Soul and I think that’s a good introduction as well.
As far as actual songs (in no particular order):
Eight Days a Week
Come Together
Help!
Yesterday!
Hello, Goodbye
Hey Jude
Penny Lane
I Feel Fine
Let It Be
Love Me Do
Can’t Buy Me Love
Being for the Benefit of Mr. Kite!
There’s really too many to list, and this was just a random selection of ones I think are decent to start with.
If I had to pick a single song, it would depend on the kid. I’d ask about their tastes and go from there.
With nothing to go on, it feels like **Paperback Writer **would be instantly accessible and kinda quirky given the subject matter, so might pique a kid’s attention.
I think the early and middle Beatles albums are a bit rough to the modern ear. Things like Twist and Shout (yes, I know it’s a cover) and even up to Rubber Soul often sound pretty dated. I’d actually start with Sgt. Pepper’s or perhaps Abbey Road (White is too experimental, Yellow Submarine is a bit weird). They both sound largely like modern albums. The Abbey Road Medley, despite being long, has aged quite well in particular, especially the Golden Slumbers/Carry That Weight/The End section. Let It Be (from the next album of course) is also still a pretty modern sounding slower rock song. She’s Leaving Home works well for that too.
After that point, giving a selection of their early and middle stuff like Eight Days a Week and their really weird stuff is a good idea, but I think it’s best to lead with the more modern sounding songs (which is fairly easy because Sgt. Pepper pretty much codified what a “modern album” sounds like). I mean, nobody is going to mistake it for post-grunge rock, but still.
I think Help! or A Hard Day’s Night (the movies) would be a really good introduction to The Beatles and their music. Part of why their popularity has endured is each member’s distinct personality and their interaction with each other. You can’t get that by just listening to the songs.
I’m 34, but only got into the Beatles in my late 20s. It’s all highly variable, but my favorite songs are:
We Can Work It Out
Eleanor Rigby
Let it Be
Ob-La-Di, Ob-La-Da
Here Comes the Sun
Can’t Buy Me Love
Help!
Across the Universe
Lady Madonna
With a Little Help from My Friends
I Want to Hold Your Hand
Sgt Pepper’s Lonely Hearts Club
Ticket to Ride
As long as the kid has never actively listened to a Beatles song before, best that he starts off with:
Why Don’t We Do It In the Road?
Her Majesty
Act Naturally
Revolution #9
You Know My Name (Look Up My Number)
Within You Without You
Wild Honey Pie
Octopus’s Garden
Don’t Pass Me By
Helter Skelter
Upon reading the OP, I thought of various answers, including “Have the kid watch A Hard Day’s Night” (as blondebear suggested), “It depends on what kind of music the kid normally listens to (and how musically adventurous he is)” (WordMan’s approach—and by the way, your one song suggestion is not a bad one at all), “Have the kid listen to Abbey Road” (It is, as Jragon said, a more “modern”-sounding album, and includes key contributions from all four Beatles), “Have the kid listen to one of their compilation albums” (as WordMan and oft wears hats suggested), or even, if you can get him to do so, “Have the kid listen to the Beatles’ entire output, from earliest to latest, and give you his reactions” (as SDMBer Satuderhorse did a few years ago).
I agree with others that this is difficult because it depends on the kid’s tastes. My youngest is 18, and has liked the Beatles for several years, specifically Sgt. Pepper and Abbey Road.
My oldest, at 26, likes A Hard Day’s Night.
I try to get people to listen to the Christmas Album all the way through, because that showcases their entire history from silliness in the Love Me Do days to the bizarre Magic Christian era.
Dude. 
Nice summary, Thudlow. I guess that’s the point: you have to gauge the kid’s interest in Music. If the kid seems into music - in the uniquely passionate way some teenagers are - well, it’s different. You’d want to check in about how aware they are that The Beatles are Ground Zero for the emergence of Rock as a mature form. If they get that and want to understand it, then you should start with their full statements - a whole album like Rubber Soul or Abbey Road, or the first movie.
If the kid is smart and interested in music, but not especially geeky about it, then a compilation CD like the Red one or the No. 1’s seems smart.
I Saw Her Standing There is the greatest three minutes in rock and roll. Nothing essential has been added to rock music since.
My introduction to the Beatles, many decades ago, was the Red and Blue albums. So, I’d start there.
I don’t recommend just one song, that can be hit or miss. I vote for the Red Album, 1962-1966 Greatest Hits. These songs were all composed by them - no covers. These early works are what launched them into greatness. 1962–1966 - Wikipedia. The Red Album captures their youthful innocence.
I’m 55 and have fun memories of listening to that album with my sister and brothers as teens growing up in the 1970s.
It was an essential part of our Sunday morning breakfast soundtrack with my kids over the past 15 years. Same fun memories - the kids love the Beatles and used the Red album as their gateway.
Should make it the single b/w Rain.
I don’t believe one can fully appreciate the Beatles by only listening to their later stuff (although of course there’s plenty of good music in the later albums). I get terribly frustrated when I run into people who seem to think that the White Album is the only one worth listening to.
With that in mind, the Red Album’s not a bad start. However, the Beatles had a number of great compositions that are virtually never played on the radio and seem to be consistently overlooked in general. It’s a shame, I tell you.
Add these to the list:
Ask Me Why
Not a Second Time
This Boy
If I Fell
Things We Said Today
You Can’t Do That
Yes It Is
ETA: I’ll Follow the Sun
The Red and Blue albums.
The first Beatles song I fell in love with was “I Should Have Known Better”. I’d say start the lad off with watching “A Hard Day’s Night”. He’ll be introduced to some good songs, meet the members, and see some Beatlemania.
The problem with recommending songs is that you miss out on the experience of the album in its totality. Give him Revolver or Rubber Soul and say; “Listen to the whole thing”.