Back in 1998 (an astonishing 20 years ago), I saw Neil Finn play a free outdoor concert in Boston.

His first solo album, Try Whistling This, had just come out, and true to its title, it was a surprisingly difficult record to love. Finn gamely tried out this new material on the Boston audience, but save for the singalong “She Will Have Her Way,” it was rough going. But then, near the end of the show, Finn pulled out an acoustic guitar and started playing “Don’t Dream It’s Over,” and the crowd came to life. Even me, the guy most willing (especially as a young’un) to champion the difficult material. I felt a stirring within at the opening chords of that song, and sang along like my life depended on it.

It’s not just that “Don’t Dream It’s Over” is a better song than anything on Try Whistling This, although it certainly is. It’s not even that it’s more immediate, and thus far easier to love. For me – and I suspect for a lot of people on the lawn that day – it was that I first heard “Don’t Dream It’s Over” in 1986, and fell in love with it then, and that love has not abated through time and tide. It was not the first Neil Finn song I heard. Believe it or not, that was “World Where You Live,” which I saw Crowded House perform live on MTV. But it was the first one I fell head over heels for.

I was all of 12 years old when Crowded House’s first album hit the American airwaves, but I like to think I knew good songs when I heard them, even then. That album is full of good songs, and it sparked my lifelong admiration of Neil Finn. By the time I was making my own money and could buy records on my own, Crowded House had become a favorite, and I’d started tracking down Finn’s older work in Split Enz. I still think Crowded House’s Woodface is one of the best and most underrated records of the 1990s, and Together Alone isn’t far behind. In fact, the first Finn album I bought and didn’t immediately love was Try Whistling This, which Finn gamely tried to sell me on during that Boston concert.

For those of you rushing to Google, don’t worry, this isn’t a eulogy. This is a straight-up review situation, but I wanted to talk a little bit about how having a long history with a performer or songwriter colors one’s expectations and reactions to new work. Finn just happens to be one of the artists whose work has impacted me for the longest time, and he happens to have a new record out with his son Liam, which I swear I will talk about soon. But mainly I want to talk about what goes through my head every time Neil Finn announces a new record, or releases a new song, which is nothing less than my entire history with his music.

For instance, I think about One Nil, his glorious 2001 solo album, and how, before last year, “Turn and Run” was the last Finn song to make me shiver and well up. I have reservedly liked everything he’s done outside of Crowded House (except for that wretched Pajama Club thing), but haven’t felt that “oh my GOD listen to this melody how PERFECT” feeling since 2001. And I’ve often wondered if the material Finn has released since then just hasn’t been as good, or if his earliest work has just burrowed deeper. It’s hard to know.

I think about how much of Finn’s work includes (and in fact revolves around) his family, for better or worse. His brother Tim was the main voice of Split Enz, joined Crowded House for Woodface, and made two records with Neil as The Finn Brothers. His wife Sharon has played with him in various bands (including that awful Pajama Club thing, of which we will speak no more). And literally the only reason I keep buying Liam Finn’s work is because he is Neil Finn’s son. He’s pretty good – much more interested in electronics and atmosphere than his father – but he wouldn’t be on my radar without my connection to his father.

And of course, I am now thinking of Out of Silence, last year’s under-the-radar record, which contained the best music Neil Finn had made in at least 15 years. And I’m thinking about how I might not have bought it, or even heard about it, if I hadn’t fallen in love with Finn’s work back in my preteen years. Out of Silence is amazing, full of gorgeous orchestrated wonders, and it’s proof to me that he’s still one of the very best, when he wants to be. It also sets expectations higher for his next project.

Which, of course, brings us to Lightsleeper, Neil’s first collaboration album with Liam. I have done my best to manage my hopes for this – all it needed to do, for me, is balance out their styles, offer up some Neil Finn melodies alongside the Liam Finn soundscapes. And blessedly, following a messy opening trilogy, it does this. It’s impressive how well the duo meshes. But I have to emphasize that, had this not been a Neil Finn project, I probably would not have listened to it more than twice. It is only the long tether of my love for Neil’s work that is keeping me attached to this album, still diving through it, still teasing out its joys.

Because they are there. I almost shut down during the formless “Meet Me In the Air,” which (save for a brief prelude) opens the album with floaty meandering, and the silly “Where’s My Room” goes on for an eternity, mutating into an orchestrated five-car pileup that did not bode well for the rest of the record. But keep listening, because the following eight songs range from the simple and pretty to the delightful, and are worth digging through.

I like so many things about those last eight songs, but what I think I like most about them is the push-pull of Neil and Liam’s sensibilities. Some of these songs, like the kinda-funky “Ghosts,” feel led more by Liam, and “Listen,” one of only two songs solely written by Neil, could have fit on Out of Silence nicely. But when Neil’s piano is given equal weight with Liam’s penchant for sonic frippery, magic happens. “Any Other Way” is a treat, Mick Fleetwood’s drums and Liam’s synths making room for a classically beautiful melody line, sung by Liam. “Back to Life” is a simple tune, but it’s a really pretty one, with a strong and memorable chorus, and Neil digs into it joyously.

I’m also a big fan of the way this record ends, juxtaposing the relatively grand-scale “We Know What It Means,” sung by Neil (with just a wonderful piano solo in there too), with the gorgeous lullaby “Hold Her Close,” sung by Liam. These are both graceful little songs, and like most of Lightsleeper, they’re subtle – you have to listen more than once to really hear how well-crafted they are. And without my lifelong love of Neil Finn, I might not have done so. I might have listened once, filed it away under “not bad,” and kept on with my life.

Which is interesting to me. I’ve found a lot to love on Lightsleeper, but I’ve only given it the repeated listens and chances I have because Neil Finn’s name is on it. This raises a couple questions for me, most notably whether I am missing similar pleasures on albums that do not have Neil Finn’s name on them, albums I pay only cursory attention to. I buy such a volume of music that it sometimes takes a 30-plus-year association with an artist’s work to get me to really listen more than once. I’m in constant risk of barely hearing songs that could change my life. It’s something worth thinking about.

But I’m also using Lightsleeper as an excuse to celebrate those 30-plus years of letting Finn’s music into my heart. I still believe he’s one of the world’s best living songwriters, and at age 60, he’s still proving it. Lightsleeperis indulgent, for sure, but in its heart live some beautiful little songs, and I’m very glad to have heard them. Neil Finn’s music has been with me for most of my life, enriching it all the while, and that’s why I will give everything he does more than a fair chance. I owe him at least that much.

Next week, the dream of the ‘90s is alive and well. Follow Tuesday Morning 3 A.M. on Facebook at www.facebook.com/tm3am.

See you in line Tuesday morning.