Cowboy:
Mac-#5 is To Make You Feel My Love,originally Bob Dylan,recent cover by Garth Brooks.
Yep, you got it (that was me, not Mac, though). Billy Joel also covered it, in fact, his version was released even before the Dylan album that contained the tune.
COMF:
but you surprised me twice: by knowing the relatively obscure Dovovan tune,
I didn't think Hurdy Gurdy Man was that obscure. Donovan was one of my favorites as a teenager, so I may be biased, but that song was one of his biggest. It was a huge radio hit at the time it came out, as I recall. Hasn't gotten as much airplay as some of his others in the intervening years, though.
and by not knowing two other very well-known, often-played songs by famous rock bands of the sixties/seventies.
Guess you'll have to remain surprised, then, because even with the additional lyrics, they don't ring a bell. For a second, I thought #2 was
Wrapped Around Your Finger by Sting/the Police/whoever, but on second thought, I don't think it is. Like you, I'll probably slap myself on the head when I find out what they are.