Sony’s deal with Michael Jackson is really kind of hilarious when you think about it. They sign him when he’s reached enormous heights of fame and popularity! So they pay him accordingly.
Only - where does he go from the pinnacle?
Why downward, of course.
Even the Beatles didn’t last forever.
Can you think of an artist who signed a big contract such as his and actually delivered on it?
Depends on how you define a big contract.
I certainly don’t think that anyone regrets signing Springsteen or Billy Joel at their “pinnacle” in the in the 70s considering the heights they hit in the 80s.
Neil Diamond, before leaving his Uni/MCA days behind, racked up plenty of Top Ten singles: “Song Sung Blue” hit #1 and went gold, “Cracklin’ Rosie” hit #1 and went platinum – heck, everything from “Sweet Caroline” to “Holly Holy” hit platinum. And maybe most of the songs people know him for come from this era, when he was charting with “Girl, You’ll Be A Woman Soon” and “Play Me” and “Cherry, Cherry” and “Kentucky Woman” and “Solitary Man” and “Brother Love’s Travelling Salvation Show” and “I Am, I Said” and plenty more besides.
In '72, he cranked out both yet another album that went platinum and yet another album that went multi-platinum; that’s a heck of a year. In '73 he signed with Columbia – where he cranked out more than twice as many platinum albums and more than twice as many multi-platinum albums.
Green Day signed onto Reprise Records in 1994 and had a major hit with Dookie!; in 2004 they released American Idiot, on the same label, and were soon playing stadiums.
Frank Sinatra started out big as a young singer, but faded. His record companies (Columbia and MCA) dropped him. Capitol signed him and he went on to ever more success. Then he moved to Reprise Records and continued his long-term success. He retired, then came back and did just as well. At the time of his death, he was still putting out successful albums.
R.E.M. were indie gods and broke through to mainstream success with 1987’s Document, with the hit single “The One I Love.” They left I.R.S. Records and signed a massive contract with Warner Brothers. The subsequent releases: Green, Out of Time, Automatic for the People - were massive critical and commercial successes. (Of course after that, R.E.M. has been considerably less successful, but three albums that were even greater than Document has to count as a pretty good return on investment - and it’s not as if even a underwhelming R.E.M. release doesn’t garner tons of attention.)
I might also add Hall & Oates to the list. They had a hit with “She’s Gone” when they were signed to Atlantic, but it actually did better as a cover version by another R&B group - can’t remember who, exactly. They signed to RCA, and they ruled the mid-80s. The RIAA has certified them as the most successful duo in rock 'n roll history.
Michael J. Jackson.
First with the Jackson 5, then his solo career which dwarfed even the very successful J5 days.
Nirvana got signed to a major deal and delivered Nevermind and In Utero.
Pretty good. In fact, it must have been a huge surprise just how good they were.
John Anderson had a lot of hits in the late 70’s or early 80’s. He then revived his career and had a lot of hits again in the early to mid 90’s.
Radiohead signed a six-album deal with EMI back when they were still called “On a Friday.” EMI probably felt pretty happy with that investment after their first album spawned “Creep,” a Top-40 smash hit.
When “The Bends” turned out to be more of a slow-burner, sales-wise, EMI brass probably figured their one-hit wonder signees had paid dividends, but were on their way out. Of course, “The Bends” has since gone on to become possibly the most-influential rock album of the 90s, and was followed up with two consecutive top-selling records, “OK Computer” and “Kid A.” The two albums that came out afterward did less well, comparatively, but both still debuted at the top of the charts. All six albums ultimately won massive commercial and critical acclaim - the latter of which, if anything, only grew as time passed.
Not bad, for a band that was only signed after the bass player randomly ran into an EMI rep at a record store.
Justin Timberlake. 'N Sync was about as big as it gets. Then he went on to an even bigger solo career. Although after some Googling, it appears that 'N Sync and JT both released their albums through Jive records - so it may or may not have been under a different contract.
ETA: As big as it gets may be a bit of hyperbole. But they were big none the less.
Johnny Cash. Huge country star but a bit faded and then hooks up with Rick Rubin and American Recordings and becomes…what? An immortal icon? Somehow the hyperbole seems appropriate.
Funny thing is, R.E.M. covers both ends of the spectrum in this topic. As the above quote shows, the initial signing to Warner Brothers was a great investment (indie stars go on to release 3 consecutive quadruple-platinum albums(“Out of Time”, “Automatic For The People”, “Monster”) (US sales of 4 million+). However, Warner’s resigning in 1996 for $80 million (at the time the biggest record contract in history) has been a bust so far. For 80 million, Warner’s got “Up”, “Reveal”, “Around The Sun”, and “Accelerate”, each of which sold fewer copies than the previous release. The last two haven’t even gone gold (Sales of 1/2 million). While “Accelerate” got good reviews (and is a damn good album), it wasn’t a commercial success. To be fair the 2003 greatest hits package did sell quite well. In the US they’re going back to being a well-regarded cult band. I’ve heard they’re still big in the UK, but I don’t know if that helps Warner Brothers or not.
Aerosmith and Jimmy Buffett both had pretty impressive second acts to their careers. Buffett’s recording career never overtook his 70s success, but his touring career sure did.
Sting’s solo career was a bigger deal than his Police career, I think.
This is a good point, and I couldn’t remember if the HUGE contract with Warners was in 87 or later. R.E.M. has gotten much more popular outside of the US as their career has progressed… I imagine when they were recording Fables of the Reconstruction in London in 1984, they could have walked down the street naked and not gotten arrested.
I think the round of massive resignings around this time (Janet Jackson, Madonna, f’rex) all backfired. I’m pretty sure all of these artists peaked commercially before the big big bucks came in.
This is what I was coming in to mention. I remember buying loads of second hand Cash albums for next to nothing, and most of my friends thinking I was crazy to buy that “country crap” - until I played “A boy named Sue”, or “San Quentin” for them. A year or two later, the first American Recordings album came out, and Cash was cool as shit. 
I remember being embarrased that I still liked Bon Jovi, then all of the sudden it was cool to like them again. Still waiting on that Rick Springfield revival.
Toby Keith was moderately successful from his first single “Shoulda Been A Cowboy”, but sometime after he released “How Do You Like Me Now” he suddenly became one of the top country singers in the business.
Comedian George Burns was big for decades Burns & Allen, then faded away after Gracie Allen retired. After the movie “The Sunshine Boys”, he was suddenly a very in demand comedian for live shows and on television up into his 90s.
The Grateful Dead. Well, they didn’t get HUGE again due to Jerry’s death, but they were coming back in a real way, if I remember correctly.