all their wars are merry

Top 5 Irish Songs (traditional):

5. The Wild Rover
Like most of the songs on this list, The Wild Rover stimulates the listener's sense of irony first and foremost. It's a popular pub song about a penitent guy who swears he's given up drinking and rambling, and then proceeds to carry on incoherently about all the good times he used to have in bars. As you will surmise, his sincerity is questionable.
only in jest

4. Finnegan's Wake
Again with the irony, which is at its most subtle (which isn't saying much) in the fact that Finnegan isn't even dead at the end, and at its most direct in the chorus line "lots of fun at Finnegan's Wake." Adapted by artists ranging from James Joyce to Dropkick Murphys for any number of diverse yet uniformly foul purposes, the song's continuing popularity is self evident.
a row and a ruction soon began

3. Whiskey You're The Devil
A song that combines two important traditions of Irish music, the ode to the drink, and the military march. Whiskey You're The Devil is known for its sing along chorus (I saw a play once that required it of the audience) that begins with the titular declaration, but ends "whiskey, you're me darling, drunk or sober," and is considered appropriate for the entire family in nearly any social situation.
sweeter, stronger, decenter

2. Eleanor Plunkett
A hauntingly beautiful harp-based tune by Ireland's revered composer Turlough O'Carolan, this song epitomizes, to me, the softer, more elegant side of Irish traditional music. Though sometimes more known for the drinking songs and comedic ditties, the true adherents of this music are often more interested in its more thoughtful, poetic traditions; its songs of mourning, and of longing.

1. The Irish Rover
And on that note I return to the raucous, and to the ironic: an upbeat and catchy tune about a glorious ship that sinks, killing everyone aboard (save the narrator). Despite that, it's an incredibly fun song, and one that has been appreciated by numerous modern bands.
fighting Bill Tracy from Dover

Part II: Top 5 Irish Songs (modern):

5. Theme from Harry's Game - Clannad
Mystical, ethereal, ponderous, yet also carrying very grounded political motivations. This is the essential Clannad track, and holds many of the virtues that have become popular in modern Irish music in general.

4. The Fields of Athenry - Pete St. John
A tale of crime and punishment with strong political undertones (listen, it's all politics from here on out), told with incredibly clear images and potent emotions. Despite its broad appeal and iconic status, this is an intimate song, a lament between lovers. It is this balance that makes the song a classic.
we had dreams and songs to sing

3. Dirty Old Town - Ewan MacColl
A charming song of earnest reminiscence, with lyrics that are part nostalgia, part rebellion and part imagist poetry. Though it has become ingrained in Irish culture, and associated with Irish music, I should confess that is not actually an Irish song, as its author is of Scottish decent, and it refers to a town in England. This should be the only one like that that slipped in; I was tempted to use Fairytale of New York (see my earlier entry on duets) again, but I figured that a song by a London based band about an American city would be going too far. Incidentally, that song's female vocalist Kirsty MacColl is the daughter of this song's author.
a big sharp axe

2. The Town I Loved So Well - Phil Coulter
Another bittersweet mixture of nostalgia and political outrage, Coulter places his good memories side by side with the bad, creating a movingly real experience for the listener. Rich detail, plainspoken and forthright emotion and palpable anger make this an epic of modern Irish music.
what's lost is lost and gone forever

1. Danny Boy - Fred Weatherly
Again, not actually written by an Irishman, but a song so pervasively associated with Irish identity that its assent to this space on the list is very nearly obligatory. It also helps that I like it a lot...
though soft you tread

By the way, does anybody else have an irrational hatred of Freezepop? I heard an interview with them on NPR the other day and was interested for the first few minutes, because quite frankly I hate so many bands that I had honestly forgotten that this was one of them, until those two brats started talking. I say it's an irrational hatred because it really has very little to do with their music per se, but I guess something about imitating artists I love and then intentionally marketing your music to people who have never heard of the real thing just ticks me off.