Playboy - Gene and Debbie 
Hey boy, to me you're just a playboy
Never meaning what you say, boy
(He spends the rest of the song trying to convince her otherwise)

Playboy - The Marvelettes
Well, you ain't saying nothing in my book
'Cause this is the one fish you'll never ever hook
You left the others standing with their hearts in pain
And now you're coming around trying to do me the same

Two Faces Have I - Lou Christie
I pretend that I'm happy
But I'm Mr. Blue

The Great Pretender - The Platters
I seem to be what I'm not, you see
I'm wearing my heart like a clown
Pretending that you're still around

Of course the grandaddy of them all used to be American Pie by Don Mclean.  For many years he refused to explain what the lyrics meant, but in 2015 he sold the original manuscript and included catalogue notes which explained the meaning of the song.  He revealed more details when the documentary The Day The Music Died was released in 2022.

Taking a cue from Aflem's message about the identity of "Mother Mary" in Let It Be, I began thinking about other songs where some (or many) of the lyrics were ambiguous as to their meaning.  

Here are a few examples.  Do you have others to add?

The Wonder Of You - Ray Peterson, Elvis Presley
"You give me hope and consolation
You give me strength to carry on"
Speculation has centered around who "you" is.  The writer of the song (Baker Knight) confirmed that he wrote it as a gospel song, and "you" was indeed the Lord.

I Started A Joke - The Bee Gees
"Till I finally died which started the whole world living"
Speculation about whether that lyric is a reference to the religious events celebrated during Easter weekend.
The Gibb brothers never clarified - they said they would leave it to people's own interpretation.

Along Comes Mary - The Association
Was Mary a reference to marijuana?  The writer, Tandyn Almer, says it was.

Louie, Louie - The Kingsmen
Did the lyrics to this song contain obscenities?  The original, written in 1955 by Richard Berry, did not have any questionable words, but when the Kingsmen released their version in 1963 with garbled lyrics, speculation was rampant that there were obscenities in the the Kingsmen's version.  Two FBI investigations concluded that the lyrics were unintelligible and not obscene.

 

What are some of your favorite LIVE - not lip-synched or pre-recorded - performances that you can share with us via video?  They may be from back in the day, or perhaps more recent (as shows such as TJ Lubinsky's PBS Doo Wop series have extended the careers of many 50s, 60s and early 70s artists).

Here are a few of mine:

Cilla Black - Alfie  (live recording session)
I love this video because it takes us back to a time when recording was a live performance, not a bunch of pre-recorded segments and vocal overlays constructed in a studio. The orchestra, backup singers, and musical director Burt Bacharach all work together to turn out this amazing performance.  You can feel the intensity of Bacharach as he guides and shapes the session. as well as experience Cilla putting everything she can into her vocals.  Bacharach, ever the perfectionist, demanded 29 takes.  Cilla said. "It was ever so difficult. The range in it was unbelievably hard.  It was hurting me".
https://www.youtube.com/watch?v=glpIgnmKrZc

Jerry Butler and Betty Everet - Let It Be Me (from one of the first PBS Doo Wop shows)
The backstory to this video contributes to making this such a special performance.  Apparently Lubinsky had been trying for a long time to get Everet to be one of the performers on his second Doo Wop program, but she had retired and was having major health issues. Finally, with Jerry Butler supplying some encouragement, she reluctantly agreed to perform.  If you watch this touching video carefully, you see how nervous she was, but also how supportive Butler is, holding her hand and seemingly singing directly to her.  At the end, she gives him a gentle nudge, as if to say, "We did it!"
Betty Everet died a few months after this performance.
https://www.youtube.com/watch?v=7RJSTBCPWYk

 

I agree that the ending of Bridge Over Troubled Water definitely sends a chill.

After going back to listen to it, two other song endings came immediately to mind, both with amazing vocals leading into an instrumental crescendo:

Ebb Tide - The Righteous Brothers
MacArthur Park - Richard Harris

As a segue from a very specific kind of song ending (the instrumental Cha Cha Cha), I would like to know what your favorite song endings are.

Here are a few of mine:

Several Roy Orbison songs have an amazing ending that builds with his unique voice ascending (sometimes along with background singers) into an orchestral crescendo.
Running Scared
Crying
It's Over

Fred Johnson hitting that deep bass note at the end of Blue Moon by the Marcels

The "Shooby-Doo-Bop-Bah-Dah at the end of What's Your Name by Don and Juan 

Joey Vann's extended and distinct expression of the words  "You Belong To Me" at the end of the song by the Duprees

 

I'm looking to make a list of songs that end with an instrumental "cha cha cha". 
Best example would be the ending of It's Now or Never by Elvis.

Not looking for the words cha cha cha in the song, only the Cha Cha Cha instrumental ending.

A few to get the list going:

Oh Carol - Neil Sedaka
Norman - Sue Thompson
Calcutta - Lawrence Welk
Sway - Bobby Rydel
Wheels - The String a Longs
Easier Said Than Done - The Essex
I've Had It - The Bell Notes

What are some of the songs that you would consider to be "guilty pleasures"  - songs that you are somewhat embarrassed to admit that you like?

Here are three of mine:

Calcutta - Lawrence Welk
Is there any person or show more unhip than Lawrence Welk?  If you are in any doubt, check the video, especially the audience dancing.  And yet I continue to enjoy this song.  Maybe it's because it brings back childhood memories of my parents watching LW faithfully every Saturday evening.  And with only one TV in the house and few channel/network choices, it was join them or don't watch TV at all.
https://www.youtube.com/watch?v=Tq0-mSIrllA

Mr. Custer - Larry Verne
In this age of political correctness, it's uncomfortable to say you like Mr. Custer.  From the war-whoops at the beginning, to phrases such as "there's a redskin awaitin' out there, just fixin' to take my hair" and "they're runnin' around like a bunch of wild Indians", there's no way this song would ever be recorded today.
And yet it brings a smile to my face every time I hear it.  Kind of like being told a joke in poor taste but you laugh anyway. 
https://www.youtube.com/watch?v=QxuBxNRsjgY

Sugar, Sugar - The Archies
I hate bubble gum music with a passion.  Sugar, Sugar is the one exception. I don't shut this song off when I hear it.  Maybe it's because I'm an Andy Kim fan and I've seen him perform it live many times.  Or maybe it's because whenever it comes on the car radio, I catch my wife immediately singing along.  
https://www.youtube.com/watch?v=Sj0pzxGyvUQ

Just heard this British instumental that I have never heard before.  If I had, it might have made my top-ten list.

Scarlett O'Hara - Jet Harris & Tony Meehan
https://www.youtube.com/watch?v=H2ePG1LWGIM

Is this Oldies Board now expanding its scope to include songs from the 1980s as oldies?

Oh Donna - Ritchie Valens
Written for his girlfriend in high school, Donna Ludwig

Peggy Sue - Buddy Holly
The song, written by Jerry Allison, Norman Petty and Buddy Holly, was originally titled Cindy Lou (Holly's niece). but was changed to Peggy Sue by Allison in an attempt to win the favor of Peggy Sue Gerron, who became Allison's girlfriend and wife.

Sheila - Tommy Roe
Tommy always tells this story when he performs it live.  He wrote the song for a high school friend, Frita. but the producers didn't like the name.  Tommy's aunt Sheila was visiting when he was told to change the name, hence the title. 

You're So Vain - Carly Simon
Probably the most famous song in this category.  For years everyone was guessing who was "so vain", until Simon finally revealed that Warren Beatty was the one she was singing about.

Oh Carol - Neil Sedaka
Sedaka claims he dated Carole King and wrote the song for her.  Howie Greenfield was actually the lyricist, so maybe he gave Greenfield the initial idea and Howie took the lyrics from there.  Interesting that Gerry Goffin decided to write an answer song titled "Oh Neil" for his wife (Carole King).

Sweet Caroline - Neil Diamond
Diamond used to tell the story that Caroline Kennedy was the inspiration for the song.  Years later he claimed it was actually about his wife, Marcia Murphey, but he couldn't rhyme Marcia (and needed 3 syllables) so he used Caroline instead.

Tricia Tell Your Daddy - Andy Kim  (A somewhat obscure reference - only made it to #110 on the Billboard charts)
The song was actually written by Jeff Barry and Marty Sanders (Jay and the Americans)
It was a direct plea to Richard Nixon's daughter to help in the peace effort.
 

Two more to add to my list:

Randy and the Rainbows
Had a #10 hit with Denise in 1963
https://www.youtube.com/watch?v=K7Xy8XLKwec

Their follow-up was Why Do Kids Grow Up - same song, different lyrics
Only got to #97 on the charts
https://www.youtube.com/watch?v=0HMuFg_aHZg

Bobby Picket
Monster Mash reached #1 in 1962 
https://www.youtube.com/watch?v=C6UI8TTIhwE

The follow-up was the same song but with Christmas lyrics - Monster's Holiday.
It reached #30 on the charts
https://www.youtube.com/watch?v=_BEB49GBiYE

Quarter To Three - Gary U.S. Bonds
https://www.youtube.com/watch?v=YF69PoyXskY

Memphis - Johnny Rivers
https://www.youtube.com/watch?v=qDG7ZdfBFRU