Here’s another anecdote/data point. In June 1969 - roughly 7-8 weeks before Woodstock - I saw The Who and opening act Joe Cocker perform in St. Louis. I paid $6 for a reserved seat in the 6th row.
The Who had released Tommy maybe three weeks before the show. No one in St. Louis had even heard of Joe Cocker.
Blood Sweat & Tears had just had two monster singles with You Made Me So Very Happy and* Spinning Wheel *. According to David Clayton Thomas, “We didn’t get paid. Nobody got paid.” (Except for The Who, who demanded cash before they went on.)
As was noted in the film and the soundtrack, it was only the second public performance for Crosby, Stills and Nash, although they were known from their earlier groups.
At the other end of the scale, Sha-Na-Na was an a capella group from Columbia University that had only performed a handful of times, and was signed as a last-minute fill in.
My explanation? because I want to sucker at least 21 posters into giving useful and fascinating insights about Woodstock and talent fees. Mission accomplished. Better leave before someone wises up.
Going by all criteria mentioned in the thread, it seems like CSN&Y came pretty cheap. Their 1 album released to that point missed the top 5, but it went #6 and sold over 4 million in the US. Plus that one was missing the “Y” and a little bit of the star power from their #1 album that followed. 2/4 of the guys were in Buffalo Springfield which had released 3 studio albums plus a “Best of” collection and had a top 10 single. One of the guys was in The Byrds - they had 2 #1 singles fairly recently. The other dude was in The Hollies . Neil Young’s first 2 solo albums weren’t the biggest, but the second went Top 40/Platinum (some of this success, including the singles probably happened after Woodstock, though).
Back when I was a sound engineer, we were doing two shows by Ray Charles. The promoter had screwed up, and the house for the first show was only half full. Brother Ray (and his manager) was not going on that stage until paid in full. He only wound up doing one show, the people there for the first show wound up waiting until the second show, and a bank vice-president had to be got out of bed to issue a cashier’s check.
CSNY famously declared on stage that Woodstock was their second gig ever. They were guys who acrimoniously had left their previous bands. At the time, individuals leaving bands had virtually no track record of success on their own, Cream being the major exception. Their first album did pretty well but they didn’t have a top ten single and in 1969 singles were still crucial.
Blood, Sweat & Tears might have been the biggest name for sheer US chart success, with three number two singles. I could have seen them the year before at college, but tickets were $4.00 and I didn’t have $4.00. They would have played to maybe 3000 people. So $15,000 would have been a good payday for a top selling group.