Not necessarily the ones you like the best, just the ones you’ve spent the most money on.
I’m not sure if T-Shirts and other swag, and movie adaptations count, but I personally am counting them.
My top 5 artists:
#1 is Pink Floyd. I had all their tapes, even buying compilations just to get rare tracks, and then of course bought the Shine On set (plus a few other CDs). Even though I’ve never bought swag or seen them live they’re number 1. #2 and #3 is a tie between Dashboard Confessional and Heart. I have a few albums by them but the main money I’ve spent is in concert. I’ve seen Dashboard around a dozen times and Heart merely 5 but Heart’s ticket prices are higher. #4 is Tolkein if you count the movies, which I own on DVD and have seen several times in theatres each (plus owning the Hobbit and Silmarillion.) #5 would probably be Saves the Day. I’ve seen them enough times that I’m getting bored of seeing them in concert, as the mixture they choose to play is not my favorite songs (unlike Dashboard.)
If Coheed and Cambria continue to tour they willl probably get a place here, as they not only always play most of my favorite songs, but they also rotate amongst their more obscure ones extremely well (even moreso than Elvis Costello, whom I’ve seen twice in concert and it was mainly the same set.)
#1 has to be Keith Urban, with 2 expensive concerts, T shirts, and every CD he has put out. #2 is probably Billy Joel. #3, maybe Barry Manilow? Not sure of the other 2.
#1 - Bruce Springsteen, no doubt. I’ve seen multiple shows from every tour since Born In the USA. (If he played a 5 night stand in LA, I would probably see 3 of them.) Add in the rest of the stuff…
#2 - Jimmy Buffett. Been a Parrothead since Fingers was a mono-Reefer. Concerts, books, records, CDs, DVDs, meals at Margaritaville…
#3 - Fleetwood Mac (and related acts). Multiple concerts, T-shirts, etc. This list includes Stevie Nicks solo, Lindsey Buckingham solo, Mick Fleetwood not-do-solo.
#4 - Dave Brubeck - Tracking down copies of every recording can be expensive!
#1 for me is far and away Guided by Voices. Between 17 studio albums (many purchased twice, with one copy being an import version with bonus tracks), 4 box sets, a bunch of official bootlegs/fan club releases, and way too many singles and EPs to count. Not to mention seeing them live 10 times, the last two times driving 4 hours to do so. And I’m not even counting the innumerable side projects. According to Amazon Cloud Player, I currently have 1328 MP3s from the band.
#2 is Sonic Youth. All 17 studio albums, and bunches of bootlegs and other releases. I’ve also seen them 3 times.
#3 is probably Pavement. Despite having only 5 studio albums, although they’ve re-released 4 of them in expanded sets. I also spent considerable time, energy, and money tracking down bootlegs of theirs back before there was such a thing as a torrent. Saw them 3 times as well.
#4 is Pink Floyd. Each of their studio albums except the Division Bell, although I bought the Final Cut twice, after I lost it in a move. They’re further down on this list because I only own one bootleg and I’ve never seen them live.
#5 is harder to say, but probably Yo La Tengo, if only because I own all of their studio albums and a few other items. Unlike the 4 bands above, I was never obsessed with YLT, I just slowly collected the items over 20 or so years.
Elton John. I’m not a big fan (though I like him), but I paid a bunch to see him on tour.
Billy Joel. Again, this is skewed by the amount I spent seeing him with Elton John.
Pink Floyd. This would easily be number one if they had charged anything like modern concert prices. I think my tickets were about $10 to see them in 1972.
Philadelphia Orchestra. I had season tickets at the Saratoga Performing Arts Center for several yars.
Ute Lemper. I’ve seen her in person ($$$!) and have four of her CDs.
After that, I guess (looking at my music shelf) I have bought the most collections and CDs by Sophie Tucker, Bix Beiderbecke, Frank Crumit and George Gershwin.
Indigo Girls, Disappear Fear/Sonia, Dar Williams, Jill Sobule, Glee Cast. Lots of albums and concerts for all except Glee, which is just downloads and TV ad dollars. Honorable mention to U2, Enigma, and Counting Crows for music but no concerts.
There are some others that I love but haven’t come out with enough albums to qualify yet.
Does only music count? I’ve probably helped keep Joss Whedon, Neil Patrick Harris, and several authors and comic book writers and artists in schwag.
Any sort of artistry, although 4 of my top 5 were musicians. While #4 was tolkien I didn’t spend nearly $100 on the soundtracks to LOTR although now that I think about it, I did drop $50 on an audio version of the Silmarillion so technically he still beats most of the bands whose albums I own even by sound recordings alone. Maybe he even beats Pink Floyd as my #1 – but I’m making an executive decision that Peter Jackson deserves some of the credit for the movies, so Tolkien ties for first place with Pink Floyd now that I’ve counted the audio recording of the Silmarillion.
Thinking on it some more, Dashboard Confession now firmly takes the #3 spot, dropping Heart to a lowly #4. Since Dashboard comes around Central Florida in the holiday season usually, there have been several times that I’ve gotten tickets only to have to miss them due to can’t miss holiday plans. If I hadn’t I’d have been up to 15 or so concerts by now.
#1 is definitely the Alan Parsons Project and their various side projects. Aside from all the tours and gas money I spent seeing them live, I once paid $150 for an obscure CD in pre-Web days. So yeah, they’re top.
#2: Rush. I have all their albums, many of their DVDs, and have attended every live show that’s come near me since 1989.
#3: Trans-Siberian Orchestra/Savatage. Albums and live shows.
#4: Probably Peter Gabriel, again because of live shows.
#5: Hrm, then it gets harder. Possibly Alice Cooper or Jethro Tull. Or Weird Al. Or Assemblage 23.
The Grateful Dead and Bob Dylan are clear at #1 and #2, respectively. After that it gets a little fuzzy. I’m going to guess the Allman Brothers, Doc Watson, and Steve Earle round out the top five, but I think David Byrne and Elvis Costello are in the running as well.
I’ve seen Neil Young in concert around 15 times and Bob Dylan around 10 times. I probably own about 25% more Dylan albums than Neil’s. I won’t do the math, but suspect this would put Neil at #1 and Dylan at #2. After that, it would be much too hard to sit down and calculate…
Pearl Jam - 7 concerts, having traveled out of the region for 3 of them, plus I’ve bought at least a couple dozen cds including both studio albums and bootlegs.
Modest Mouse - 4 concerts, a t-shirt, and about a dozen cds both studio and bootlegs
Radiohead - 2 concerts, lots of cds.
Animal Collective - 2 concerts, a fair amount of cds, but I’ve dl’d most of my bootlegs, plus a t-shirt.
Led Zeppelin - No concerts, 1 t-shirt (I’ve still got it after 20 years…old tee in my collection!), plus lots of cds.
Robbie Fulks, I have all his recordings and see him every time he’s w/ in 30 miles of here. I’ve even bought some of his stuff as gifts. I bought one of his CD’s twice because i didn’t like it the first time around. But now i love him… want to have his children. Alright, I’m kidding… i’m a guy, after all He is the greatest artist of all time. I think i’d buy anything he produced.
Butch Walker (including M3), I have all his/their recordings (some i don’t even like) but haven’t seen him every time he’s near. That’s because i saw him about 5 years ago and thought it was one of the best shows ever. I don’t want to have that image tarnished, ha!
King’s X (including Poundhound), I have all their recordings and see them every time they’re in town. However, when i was younger, i traveled 100+ miles to see them.
The Tragically Hip, I have a lot of their recordings. I lost interest over the last few years, but have a lot of their music and T-shirts. Also, I’ve traveled 100+ miles to see them. Of course, being a Yank, it’s gonna be tough to see them locally, ha!
Danny Elfman. I bought a lot of OingoBoing stuff in the 80’s, but that doesn’t really cause him to rank. He has his name (soundtrack) on so many things these days, that i probably can’t even quantify how much money I’ve (inadvertently) spent on Elfman.
1: By far, The Who. Many shows going back to '78, solo gigs, albums, DVDs, books, assorted performances of Tommy, etc.
2: Probably Todd Rundgren.
3/4: Tie between Pink Floyd and The Beatles.
5: (Because I wanted to right up front on the last tour), Peter Frampton.
although now that I think about it, I did drop $50 on an audio version of the Silmarillion so technically he still beats most of the bands whose albums I own even by sound recordings alone. Maybe he even beats Pink Floyd as my 
He is the greatest artist of all time. I think i’d buy anything he produced.