I have a Jude Cole CD in my collection — A View From 3rd Street — that I inherited from my wife. The faded booklet and dated cover art make it look like it’s a couple of decades old, and that’s exactly how I thought of it when we first merged CD collections all those years ago.
But as I’m reading up on Cole, I see that CD was released in 1990, meaning when I met Alex it was essentially a new release. Of course now it really is a couple of decades old so I guess it has finally grown into my perception of it.
Some other interesting things I found out about Jude Cole on Wikipedia:
• He is Michelle Pfeiffer’s brother-in-law
• He is one of Keifer Sutherland’s best friends and was to walk Julia Roberts down the aisle had she gone through with her wedding to Sutherland
• He had a role in Better Off Dead
• He’s a contributing commentator on Extra
As for his music, it’s quite good. A View from 3rd Street is packed with great tunes, many about the falling apart of a relationship. Perhaps Keifer found some solace in his friend’s songs. ‘House Full of Reasons’ is my favorite of the bunch.
Watching the door you slammed so hard it broke the windows
Up and down I’ve climbed these walls
It seemes I’m trapped inside
This house full of reasons I should be moving on
You had me believing this is the way love goes
Off and on among normal people
Down in the hall the pictures of a happier couple
Just hang on the wall and smile away through all the trouble
Side to side
The clock on the wall reminding me by the hour
There’s a house full of reasons I should be moving on
You had me believing this is the way love goes
Off and on among normal people
All day
When it’s dark
It seems there’s nothing here but
A house full of reasons I should be moving on
You had me believing this is the way love goes
Off and on among normal people
Meet Me In Montauk 
I like what I have heard of Jude Cole. This sounds like something between Squeeze and michael Penn–worthy comparisons.