Well, since the only act I’ve seen in concert 5 times is the Moody Blues, they have to rank #1.
After that, since I tend not to buy T-shirts or any other memorabilia, it’s anybody’s guess.
#1 Robyn Hitchcock, I have nearly every Soft Boys release (including singles). Mostly on LP and CD, then solo stuff (LPs CDs VHS…). Biggest reason he wins cost wise is that I’ve seen him live more times than I can remember.
#2 Frank Zappa, I have probably less that 10% of his album/CD output, but that’s plenty.
#3 Probably Floyd, having worn out and replaced LPs then bought the same on CD plus band and solo DVDs. Also the odd poster way back when.
After that no-one stands out, Zeppelin maybe, for the same reason as Floyd, a lot of LPs replaced with CDs then added compilations, DVDs…
This is pretty tough, actually.
I’m pretty sure Beatles are #1, due to lots and lots of records and books; also, if the individual members are included, I’ve seen Paul and Ringo in concert.
Again, if individual members are counted, the Flatlanders are probably on the list; I’ve seen them in concert twice, plus Joe Ely twice and Jimmie Dale Gilmore once.
Other contenders:
King Crimson (lots of albums, saw them twice and saw Fripp in concert twice)
Asleep at the Wheel (saw them twice and Ray Benson once)
The Dead (lots of albums, saw them three times)
Dylan, Who, Jethro Tull, Kinks, Gong/Daevid Allen (lots of albums, saw each twice)
That one Van Gogh I bought really throws off my curve.
What about Serenity?
#1 is definitely Kate Bush. Besides a huge number of records and magazine articles, I’ve invested a huge number of hours building web sites, authoring DVD compilations and even flew to England to dub a friend’s entire video collection.
#2 is Todd Rundgren. Unlike #1, he tours, so I’ve traveled all over the US to see Todd shows.
After that, there is a huge drop-off. I have a very big DVD collection, but it is not dominated by one director. I have a complete set of Terry Prachett books, but I think that is the default here at the Dope.
Yup, that one too. Two times in fact, I lent out my first one, never got it back, bought another.
I still have to buy and watch Dr Horrible, though.
- Depeche Mode (Mostly due to ex-GF and about 15 concerts)
- Radiohead
- Morrissey
- U2
- The Cure
I mostly listen to Hip Hop and R&B now, but the list is from when actually spent significant money on music, concerts and related paraphernalia.
Springsteen, been going to his concerts since before “Darkness on the edge of town” came out, with the 1st concert attended being back in 1977, or possibly 1976.
He’s so far out in front I can’t even quantify my next 4.
Wow, I totally forgot that I’ve probably seen the Moodies about that many times too. Maybe more. All between the ages of 13 and, oh, 25!
I wonder how many times I paid for tickets versus my brother (the actual MB fan). I guess I’ll put them as my #5 - and the only band I’ve bought tickets to see live from whom I have not one album!
#1 by far- Prince. I am the #1 Prince fan in all of the land.
#2- Pink Floyd
#3 Mary J. Blige
#4 Sublime
#5 Mariah Carey (possibly a dingbat but the girl can sing)
If you’re in the north eastern US I strongly suspect we’ve been in the same room at least once. Wanna come over and listen to records?
For me to really list the top five accurately I’d have to do more math than I’m inclined to do. I’ve seen Lyle Lovett live a few more times than I have Eric Clapton, but most of the Clapton shows were at big venues with higher ticket prices. Pink Floyd is probably in the mix.
Robin Trower
Neil Young
Steve Earle
Jimi Hendrix
Not sure what would be #5, maybe Rolling Stones.
Not just the eastern US - I spent 20 years in Charm City. I’m betting it was more than once. 
Zappa/MoI. I probably own a couple dozen CDs. Plus books, posters, etc.
The Residents. Many CDs, posters, T-shirt.
Joni Mitchell. At least 8 CDs.
I’m envious of all of you and your Dylan and Dead shows. I was born too late, and mine is far and away Phish. 30 shows just this summer, definitely my favorite way to travel and see friends all over the country. I don’t even know what band would be second, I’ve seen most bands three or four times. All my extra money goes to live music and I don’t regret it a bit.
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Depeche Mode - all albums (most on cassette, then CD, then remaster CD), most singles, seen them live 7x, shirts
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Nine Inch Nails - all albums (one or two remasters), shirts, seen them live 4x, bootlegs
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Erasure - all albums, most singles, seen them live 2x
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VNV Nation - I’ve seen them live 8x and own all the albums and singles
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Mesh (UK) - Own all the albums and singles, seen them live 2x
Along with several other really awesome Dopers in this thread, my #1 is Pink Floyd. I have bought all their albums at least twice (every CD and all their albums on iTunes) plus I have something like 10 Floyd T-shirts, then I have seen them once (the Gilmour Floyd in '94) and Roger Waters The Wall once in 2010 (with tickets purchased to see him again in July). Plus purchasing The Wall on videotape and DVD, and others like Live at Pompeii, etc.
My #2 would probably be Neil Young, as I have purchased all his albums several times over, some in vinyl, all in CD and all via iTunes, and seen him three times.
The rest would be a tie between a bunch of other bands…
Between albums and concerts, The Who and Jethro Tull are far ahead of the rest of the pack for me (in fact I’m listening to Tull’s “Dark Ages” as I type this).
Richard Thompson is probably third. Maybe Sonic Youth fourth, just because they’ve released so many freaking albums and I’ve bought most of them.
Fifth could be any of a number of bands mentioned upthread - The Residents…Pink Floyd…hard to say. I don’t listen to those two band so much anymore, but I’ve got lots of their vinyl still hanging around.
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Without a doubt, ‘Weird Al’ Yankovic. The only albums of his I don’t have are Alpocalypse (which I do intend to get one of these days) and the various compilation albums (why bother when I have the others?)
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AC/DC. All Brian Johnson era. 2 different versions of AC/DC Live (the 1 disc version and 2 disc collectors edition), as well as several (though not all) other albums.
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Probably Guns 'n Roses. I have everything from the “real” lineup (in other words everything from AFD to Spaghetti Incident)
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I’m going to guess this one would go to John Williams, because I bought the soundtracks to Star Wars eps 1-3 back when the hype for each movie was on. I also don’t technically own but could get ahold of my dad’s copy of the original Star Wars soundtrack on vinyl. No Empire or Jedi, though.
5 (and 6, sorry). I believe this would be a tie between Metallica and Megadeth. I don’t have anywhere near everything from either band, and I’m not even that fond of everything I do have, but I just think they would come in next on number of albums I have.
I’ve also got buttloads of various WWF/WWE theme albums, so maybe Jim Johnston should be in there someplace, I dunno.