Tribe by Pete and Maura Kennedy - the Kennedys are one of those bands whose bouncy music and superficially simple lyrics hide a lot of ideas you could live by - and you can hear their love for evch other in everything they do. Tribe is definitely on the simpler end of the scale but no less true for that.
Take it from Day to Day, by Stan Rogers - I had to include a song by Stan. This is one of his songs bringing Canada's history to life - sung by a sailer onboard a ship going through the Northwest Passage, who's getting a bit sick of ice. The rhythm is entirely infectious, and the song is prone to earworming but I never mind it.
Tambourine Man, by Bob Dylan - I like the Byrds version, but I like the original better. I never have quite figured all of what it's about, but i love the image of following a traveling musician through a sleepy summer morning.
Thunder Road, by Bruce Springsteen. My all-time favorite of Bruce's - I love the ragged tune, the way the lyrics fit around its rambling corners, and the idea of running off to freedom and adventure together even when it's not in the idyllic first flush of youth. (I'm not too crazy about the line, "You ain't no beauty, but hey, you're all right," though.)
There Were Roses by Tommy Sands - Ireland. Israel, Bosnia, Rwanda. Wherever. "Those who give the orders, they are not the ones to die/ It's Bell and it's O'Malley, and the likes of you and I".
Till Then from the musical 1776 - because the intertwining melodies are beautiful and because every time I hear it I'm so entirely in sympathy with John (my work life) and Abigail (my home life).
To Live is to Fly by Townes van Zandt - Another one whose lyrics only look simple, and another of those rambling cornery tunes.
Truckin' by the Grateful Dead - College memories, long styrange trips, and Houston really is too close to New Orleans.
Turning of the Tide by Richard Thompson - For the happy rhythm and and the bleak words. Also included as a representative because unfortunately neither Beeswing nor Dimming of the Day begin with 'T'.
Turning Toward the Morning by Gordon Bok - Gordon's voice is the next best thing to Stan Rogers - or maybe better, seeing as Gordon is still alive - but before I ever heard it or the tune I loved this song because it has the most beautiful lyrics I've ever read. "The stars are swinging slow / And the seas are rolling easy as they did so long ago. / If I had a thing to give you I would tell you one more time / That the world is always turning toward the morning."