hmm for me temptation by new order
For my enemy? make them listen to “its raining tacos” by parry gripp there’s a 10-hour repeat track on youtube after listening to that you will 1 eat 50 pounds of tacos and 2 take a hammer or drill to your skull - YouTube note thats the same 2 minute song repeated for 10 hours …
Yep…see my followup post as I recognized my mistake.
Got any songs about ninjas? 
Believe it or not… A viable candidate for list two…3 minutes long and ends just before it wears out its welcome. >_> Two days of it would be…excessive.
I’d listen to “Giant Steps” for two days solid, no problem. It might take me that long to appreciate everything he’s doing.
Considering who my greatest enemy at this moment is, 48 hours of “Giant Steps” might well be pretty effective torture as well.
For me: Probably a song like The Lover After Me by Savage Garden. I like it but not too much, soft enough that I can ignore it, but not too much that it would put me to sleep.
For my enemy: I Live in a Split Level Head by Napoleon XIV
For me: “God Bless the Broken Road” by Rascal Flatts
For my enemy: Richard Harris singing “MacArthur Park”
For me I’d probably go with some sort of meditation music. Basically anything like those played here. These don’t have words and so they may not count as a “song”. If it has to have words, then possibly On your shore by Enya.
For my enemy I gotta go with Lucy in the sky with diamonds by William Shatner.
For me, probably something instrumental. I don’t think I could listen to the same lyrics for 48 hours straight. Maybe something like Camel - “Sasquatch”.
For my enemy: Unfortunately, Frank Zappa’s appropriately named “The Torture Never Stops” is too long, so I’ll go with “I Come From Nowhere” instead.
For my own 48 hours of loop, i’ll go with Pink Floyd, “Shine On You Crazy Diamond”, which I like, has long segments of instrumental music that can blend into the background, and importantly is over 26 minutes long. So I’ll “only” hear it about 110 times, and about a third of that I’ll be asleep.
For my enemy, I’ll take John Mulaney’s story of a childhood prank at the Salt and Pepper Diner for a template, and go with Tom Jones, “What’s New, Pussycat?”… But punctuated just once with “It’s Not Unusual”.
You should re-read the OP. Maximum song length is seven minutes, and you will hear it in your sleep.
For me, I’d pick some sort of ambient music, since it’s designed to be unobtrusive, something like Chihei Hatakeyama’s Sad Sea.
For my worst enemy, the guy who has ruined my life and done the most damage, the same, obviously. Listening to two different songs at the same time sounds dreadful.
My personal 48-hour song would be [del]the Allman Brothers - “Dreams” Hell, I DO sleep through it when I go to bed listening to music, and when I’m awake, I love to close my eyes and drift off on the extended guitar solo.[/del] Well shit, it’s about 7:15 long. Gotta pick something else.
I have a high tolerance for songs I like. Anything that is fairly relaxing to me will work here. Maybe something that’s an instrumental, as I find vocals distracting when I’m trying to concentrate at times. I think, “Europa”, by Carlos Santana (the live version off of Moonflower)would work, though I also considered, "The Gold Bug" by the Alan Parsons Project.
For my greatest enemy song, How shall I choose? Well, there’s a lot of ridiculously bad (from my perspective) experimental stuff out there, but that seems like a cheat. Picking some obscure song that’s barely a song doesn’t seem right.
I could pick a modern heavy metal song with cookie monster vocals, but you never know. There are a lot of ppl who love that stuff and could sleep through that.
I could pick a bad song that I hate with the fire of a thousand songs, like, “Break My Stride” by Matthew Wilder, or, “We Built This City” by Starship. That would be immensely satisfying on a personal level, but maybe my enemy has bad taste. They would, if they’re my enemy 
I think I’ll pick a GOOD song that might be rather annoying to sleep to.“Time” by Pink Floyd famously starts out with a cacophony of alarm clocks and bells, but is otherwise a fairly mellow song. I think that might be draining after 48 hours.
Oh. Oh, you are EVIL. EEEE-VIL!
I’ve been on a Bob Marley kick lately, so I’ll take Get Up Stand Up.
My enemy can *really *get to experience The Song that Doesn’t End.
I could listen to Beethoven’s 6th Symphony from now until the day I die so I’ll go with that. If it must be popular music I’ll go with When The Music’s Over or The End, either/or. EDIT: 7 minutes? Fine. Spanish Caravan it is.
For my enemy I’d go with any of the four sides of Metal Machine Music, as each constitutes a “song” of sorts and is virtually indistinguishable from the others. Go ahead, give it a shot. Your average person won’t last 7 minutes.
For my listening experience, it would be “Eye in the Sky” by The Alan Parsons Project. It’s bouncy, but sort of low-key. Some of the wordplay is cute. I think I could handle it for 24 hours.
For my enemy, it would be “Spirit in the Sky” by Norman Greenbaum. (Note the stark similarity of the titles.) I personally find it obnoxious, grating, repetitive, and just plain sucky. I can only hope that he/she will, too.
My kid listens to a lot of instrumental hippie music, almost ambient in nature. I’d ask him for ideas of stuff I could stand…
(I call the genre “We were stoned out of our gourds when we recorded this; we’re counting on you being stoned out of your gourd when you listen to it”)
Ooh, I just had a better idea. I’ll stick to Beatles songs.
I get Blackbird, my enemy has to go insane to Ob-La-Di Ob-La-Da, Revolution #9, or Helter Skelter.
After giving it some thought, I’ll pick B. T. O. 's Takin’ Care of Business to listen to on an endless loop for 48 hours. It’s been one of my favorite songs ever since it came out.
For my greatest enemy, I sentence him to listen to Seasons In the Sun by Terry Jacks.
Would be hard to listen to any song that long but I guess if I had to choose it would be Jeff Buckley - Last Goodbye.
For my enemy I would give them Paris Hilton - Best Friend’s Ass. Worst song I’ve heard in years. Ugh.