This is the fifth song I’ve featured from Wilco’s 2007 album Sky Blue Sky, all on Random Weekends. That’s nearly half of the album’s 12 tracks. The Random iTunes Fairy seems to have a thing for this record.
‘On and On and On’ is a deep cut on an album that is one of the band’s least heralded releases, but it’s quite meaningful to songwriter and lead singer Jeff Tweedy. Here’s what he had to say about the song in a 2016 interview:
The song on Sky Blue Sky that I think means the most to me is a song that never really gets that much attention and it’s “On and On and On.” I wrote it for my dad because my mom died during the making of that record. It was my attempt to write something that was comforting to my dad about losing my mom.
On and on and on we’ll stay together yeah
On and on and on we’ll be together yeah
You and I will try to stay together yeah
On and on and on we’ll be together yeah
[Chorus]
Please don’t cry we’re designed to die
Don’t deny what’s inside
On and on and on we’ll stay together yeah
On and on and on
On and on and on
[Verse 2]
One day we’ll disappear together in a dream
However short or long our lives are going to be
I will live in you or you will live in me
Until we disappear together in a dream
[Chorus]
Please don’t cry we’re designed to die
You can’t deny even the gentlest tide
On and on and on we’ll be together yeah
On and on and on
On and on and on
We’re going to try
[Verse 3]
Please don’t cry
This world of words and meanings makes you feel
Outside
Something that you feel already
Deep inside
You’ve denied
Go ahead and cry
[Outro]
On and on and on we’ll stay together yeah
On and on and on
On and on and on
You and I will stay together yeah
You and I will try to make it better yeah
Meet Me In Montauk 
So sad and poignant 🥲
Wow, what a beautiful, powerful song! I especially love the sentiment in Verse 2.