In recent months, I’ve found myself declaring a couple of times that one song or another was officially among my all-time favorites.

That got me interested, during these pandemic times, in creating a definitive playlist of my favorite songs. This is an exercise fraught with peril and subject to repeated second-guessing, but that’s also what makes it fun.

Narrowing such a list to ten songs proved impossible, so I kept at it until I had close to 30, then pared back to 25, which feels like a good number.

My list spans eight decades and is split almost exactly between bands and solo performers. Most of my favorite artists are represented, as are a couple of one-hit wonders and artists whose impact is limited to the one song.

I aimed for variety among the performers and songs, but — true to form — almost everything on my list is melancholy. I could try to force some upbeat tracks into the lineup, but that would be lying. The songs that move me most are almost always sad, or at least bittersweet.

Over the next two weeks, I’ll go through my list a couple of songs at a time. Given how much I love these songs, I have featured all of them on the blog already, so each SOTD will be a live or alternate version. I’ll link to the originals.

I stayed away from ranking these songs in any way. It was hard enough just getting down to 25. I will present them here in chronological order, starting with the four oldest tracks.

‘Have Yourself a Merry Little Christmas‘ – Judy Garland (1944)

This one should come as no surprise, as I’ve made it my Song of the Day ten times already in various incarnations. I have a special fondness for Frank Sinatra’s version, a staple from my childhood, though Old Blue Eyes really messed up by changing “until then we’ll have to muddle through somehow” to “hang a shining star upon the highest bough.”

But my favorite version is the original — Judy Garland’s performance in Meet Me In St. Louis. That preference was solidified when I saw the film last summer as part of my AFI Musicals countdown. This movie has become a favorite of mine, and Garland’s ‘Have Yourself a Merry Little Christmas’ provides the emotional climax of the film.

Incidentally, this is one of three songs on my list of favorites that was written for a movie.

‘Angel Eyes‘ – Frank Sinatra (1958)

As I alluded to in the previous entry, I grew up listening to Frank Sinatra. He was (and is) my parents’ favorite artist. My wife loves the swinging Sinatra of ‘Fly Me to the Moon,’ as do I, but I’ve always been most drawn to Sinatra the sad balladeer. Whether it’s the lonesome tale of Watertown or the saloon songs on In the Wee Small Hours and Only the Lonely, Frank was at his best when he was down in the dumps.

Only the Lonely is a gripping masterpiece, featuring a collection of classic torch songs and orchestral arrangements by Nelson Riddle. Sinatra was just 43 years old when he recorded the album, six years younger than I am now, but I’ll always hear these songs with 12-year-old ears.

‘Angel Eyes’ is the album’s richest cut, depicting a gin-soaked fella pouring out his broken heart to a saloon full of people who likely don’t give a damn. Riddle’s orchestration lends cinematic scope to the scene, and Sinatra delivers one of his best vocals. A true classic.

‘If I Fell‘ – The Beatles (1964)

Gun to my head, I would name A Hard Day’s Night as my favorite Beatles album, and ‘If I Fell’ as my favorite Beatles song. Apologies to ‘In My Life,’ which would finish a close second.

One reason I give this gorgeous ballad the nod is that it’s a lovely collaboration between John Lennon and Paul McCartney. While it’s mostly a John composition, Paul reportedly contributed the intro. And the two men sing in harmony throughout, using the same mic on the official recording.

It’s a beautiful love song, an exquisite melody, and a poignant snapshot of one of the grandest musical partnerships of all time.

‘April Come She Will‘ – Simon & Garfunkel (1965)

Paul Simon has written a treasure trove of incredible songs, many of which could easily find their way onto this list. From the folk rock of Simon & Garfunkel through his more soulful 70s output to the world rhythms of his music in the 80s and beyond, Simon is among the very best.

But the song of his I return to most of all, and the one that utterly soothes my weary soul, is ‘April Come She Will.’ Clocking in at just under two minutes, the song traces the arc of a love affair (to quote another Simon tune) through the metaphor of passing months.

I believe I first encountered this song in The Graduate, where it is used to great effect in a sequence where Benjamin Braddock whiles away his summer having an affair with Mrs. Robinson. The sadness of the song underscores the unhealthiness of that relationship.

In recent years, my love for this song has taken on a new dimension after I introduced it to my younger daughter and it became a favorite of hers as well.