- Ke$ha. I have both of her albums so far and saw her in concert last year. I also have a Kesha T-shirt. I’ve been known to take off my sweater on the train ride home from work (pretending to be too hot), revealing my T-shirt to the people I ride with. Kesha is #1 both in money spent and as my overall favorite.
- Tom Petty (four albums and one concert)
3-5 get a bit more difficult to say. Contenders include Michael Jackson, Weird Al, Chicago, and Elton John. I’ve never seen any of them in concert but have at least two or three CDs of each.
U2, Peter Gabriel, Alan Parsons Project. Not sure what would be after those three.
#1. Bob Dylan
#2. Richard Thompson
#3. Townes Van Zandt
#4. Flogging Molly
#5. About a 100-way tie.
Other than authors, musicians are probably easiest to quantify. I’ve probably spent more on certain comic titles or DVD series but they all have multiple people involved and even the writers don’t stay on for the whole series. And it’s hard to say how to count things supported by ad revenue.
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Frank Zappa. I own damn near everything he ever produced, I think. Missed seeing him live on his last tour, tho.
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The Residents. I have all their albums, used to have Bad Day on the Midway (an early video game they made), have copies of live shows, videos, short films, etc. but I’ve only seem them live in person once.
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Slayer. I own damn near everything they have ever produced except t-shirts (I only have 2). I’ve seen them live at least 6 times.
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Beastie Boys. Again, I own damn near everything they have ever produced, although the only time I’ve seen them live was on their first tour. I’ve even done a couple of remixes of their song Alive.
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The Clash. I think I actually do own everything they ever did and I saw them on their Combat Rock tour.
I may have got the order wrong on total dollar amounts, since all of that is stuff I’ve been buying for at least 30 if not 35 years.
Honorable mentions go to Devo, The Ramones and Gary Numan.
#1 would easily be Tom Petty and the Heartbreakers. I only own one album but I’ve seen him in concert something like 9 times in 3 states. Each ticket was probably between 50 and 100 dollars.
#2 I think would be Led Zeppelin. I own two box Zeppelin box sets (one was over $100), a Zeppelin tattoo, and saw Page/Crowes in concert (amazing show BTW)
#3 would probably be Pink Floyd. A couple of concerts on VHS, a bunch of now lost CDs, some posters a handful of T-shirts and saw Roger Waters in concert twice.
After that, I’m not sure. (Pre Kid-A) Radiohead maybe. Come to think of it, Marilyn Manson is probably in the #4 or #5 slot. Back in high school/college I saw him twice and owned two (I think) of his CDs.
I think Roger Waters, Marilyn Manson and Tom Petty are the only people I’ve seen in concert more then once so this list is probably about right.
#1 Pearl Jam - Only saw them twice but they were arena shows. Bought CDs, vinyl, quality bootleg tapes and traded tapes. Bought a LOT of t-shirts (one for every day of the week!) and a lot of magazines to read about them. Oh and a book.
#2 Ben Folds Five. Saw them the most of any band (including Ben solo in this), and in many different places inside and outside of Ohio. Bought some shirts. Traded a lot of tapes.
#3 Squirrel Nut Zippers. Saw them a lot in and out of the state. Traded a lot of tapes. Bought music from bands based on their recommendations.
No one else really comes close. I saw everyone else live just once, if at all. Maybe Belle & Sebastian because I bought all of their albums new. Others I have full collections of but half from the used bin.
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Richard Thompson- I’ve seen him twice live and have most of his discography.
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A Killing Dove. A local band I’ve lost count how many times I’ve seen. I also bought their first CD. Their second CD just came out- I’ve still got to get it. I used to work with these guys and we’re still friends. Do friends’ bands count?
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Ted Leo and the Pharmacists- I only have one CD, but saw them twice in concert.
4-7)Drive-By Truckers, Eric Clapton, Alison Krauss, Jimmy Buffett in some order.
Oh, wait… are we counting travel expenses and non-muscal expenses in this equasion? Because if we are, #1 for me is American Idol finalist Ace Young. I have done a shit-load of traveling to see him perform, including a trip to NYC to see in in Grease on Broadway. I also worked on a small auction/charity for him and put tons of my own money into it. So yeah, he is #1, Keith Urban #2, Billy Joel #3, and Barry Manilow at #4.
REM and U2 are definitely #1 and #2, after that it’s kind of hard to say. Morphine would have to be on the list. I saw The Smithereens probably 4 or 5 times back in the day but back then tickets to club shows and T-shirts were a lot cheaper than they are now. I may have to think about this some more. 
This is a fun thread.
No 1 is the Dutch writer Karel van het Reve. I have about half a yard of books of his on my bookshelves.
No 2 is Kate Bush. I bought all her records the week they came out and that was back when it came still out of my allowance.
No 3 is The Cure. Same thing as Kate Bush, only they came later and by then my allowance was bigger. 
No 4 is the Belgian a-capella folk group Lais.
I would like to nominate this as the most unlikely 1-2 combination in the thread so far.
Just to have some jazz guys mentioned, and based purely on numbers of records (LPs, cassettes, CDs) I have bought since the 50’s, my top 5 would be:
- Dave Brubeck
- George Shearing
- Miles Davis
- Henry Mancini
- Stan Getz
Since I did that list from memory and may have miscounted after Miles, it’s possible that (4) and (5) could be:
– Chet Baker
– Gerry Mulligan
– Charlie Parker
– Dizzy Gillespie
Ute Lemper was just in Akron but we couldn’t go. We watched about two hours of her on YouTube instead.
I’m up there with you in the Gershwin department, and I bow to no one on quality and quantity of Mills Brothers. I also have a boatload of Louis Armstrong.
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Rush - Beyond all others. Every album, live and studio - sometimes in multiple formats. Every live VHS/DVD, again in multiple formats. Personal goal of attending at least three shows every tour, including shows not located anywhere close. Have the go ahead from the wife to actually go international on the next tour. Countless t-shirts. A tourbook collection that goes back to Signals but needs completion. Have every book Neil Peart has published. And the solo albums done by all three members.
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Pink Floyd - Every album and DVD. But a lack of touring now keeps them from taking the number one spot. I was never able to see them, but was able to see Roger Waters recent Wall tour.
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Tolkein - This is a long-term achievement, I have had all the reading material I need for years. The movies I purchased before becoming completely disillusioned.
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John Scalzi - In the list based on the fact that he is a relatively young author and there has been nothing he has written that I have not loved. I have every one of his books, many signed thanks to his frequent tours and book signing events. Watched Stargate Universe just because he was a consultant for the show.
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Joss Whedon - DVD collections of too many of his shows. Always impressed by the level of thought put into his work. Of course its not always realistic, but it is almost always entertaining. Will even eventually see the new horror flick he was involved with.
Hmm…I’ve spent more than I care to admit on the musical accompaniment to this webcomic. Of course, that’s not so much one artist as a dozen under a single publisher, but whatever.
After that, it’s probably all game developers. Something like:
#2 WOTC
#3 Nintendo
#4 Asymmetric
#5 3DO
- Tom Waits
- Bob Dylan
Massive tie for 3, 4, 5.
Travelling is where I personally draw the line because the artist isn’t even theoretically seeing a cent of the travel expenses, but if you want to count it feel free.
If travelling were included, my number one would be The Promise Ring, as that’s the only band I’ve travelled out of state for. Went all the way to Milwaukee from Florida and I’m sure my travel expenses topped $500 once you include hotel.
Then again you’d also have to include the not-insignificant travel expenses to House of Blues at Downtown Disney either from Palm Bay or from the west side of Orlando (which is still 20+ miles from Downtown Disney), which might bump up Dashboard or Saves the Day back up a bit.
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Hanson - Bought all of their studio albums, their Christmas album, an album of live music, and a single. Bought a poster, a calendar, membership to their fan club, several unauthorized biographies, and their tour video. Saw them in concert four times, but I think I only paid for the tickets once, and the other three times I had a boyfriend pay for them, but they were only buying them because they knew of my long-standing love for the band, so I’m going to choose to count the tickets as well.
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Kenny Chesney - I actually don’t own any of his albums and only have a few of his songs downloaded, but I bought two tickets to go see him in concert last summer, and two more to see him again this summer.
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Newfound Glory - Bought three albums, one single, one t-shirt, and then bought one album over again when the CD started skipping.
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Dada - Bought five CDs.
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Bryan Adams - Bought four CDs.
Oh yes, I forgot Whedon. I own 7 seasons Buffy, 5 seasons Angel, 2 seasons Dollhouse, , the only season Firefly.