The Times reported that rapper Jay-Z is about to close a $150 million deal with concert promoter Live Nation, and said, in its headline, that the deal is a "New Model For Ailing Business." Really? Because the whole thing sounds awfully familiar.

A ridiculous amount of money spread over a ridiculously long contract (10 years), check. A star who seems to have peaked, at least for this celebrity cycle, check. A vanity record label, check (granted, Jay-Z has actually helmed a record label, so the level of vanity is debatable).

This whole thing would be straight out of the 1990s, when many such deals were signed only to later go sour, if the artist were signing with a record label instead of a concert company. But even that wrinkle isn't fresh since Madonna got there first.

Props to Jay-Z for signing a mammoth deal before such arrangements become extinct forever, but the future of music is probably going to look a lot less blingy than this. Picture hundreds of thousands of smaller acts making modest coin of iTunes sales and small concerts.

Anyway, here's a look at all the big record deals that came before Jay-Z's, and that now look a bit less impressive:

Via this ABC News gallery:

  • Madonna, $120 million over 10 years with Live Nation. October 2007.
  • Michael Jackson, $108 million for six albums. 1991.
  • Janet Jackson, $80 million for for records. 1996.
  • Mariah Carey, $80 million for four albums, 2001.
  • Barbara Streisand, $80 million. 1992.
  • REM, $80 million for five records, 1996.
  • Metallica, $60 million. 1995.
  • Prince, $100 million. 1992.
  • Whitney Houston, $100 million. 2001.

Times: In Rapper's $150 Million Deal, New Model for Ailing Business