We asked the singer-songwriter—whose new musical, Spring Awakening, previews at Lincoln Center this week—to re-spend his first BMG publishing contract.

The celebrity matchmaker was once promised that much by a client if she introduced him to his future wife. (She collected.) Now that she’s also a TV producer and a novelist, Daniels calculated what she’d do with the cash today.

The artist-designer-author—and mother of CNN’s Anderson Cooper—plays with the price of a collage (plus tax) from her current exhibit at the Andre Zarre Gallery.

The R&B star’s “1 Thing” is the single of the year so far, and her second album, Touch, just dropped. We asked her to spend the song’s iTunes earnings to date.

We gave the Knicks president the starting salary for NBA rookies— in theory, of course. Here’s how he spent it.

We gave R.E.M.’s lead singer the price of the band’s first touring vehicle —a 1982 Dodge van—and a tank of gas (in play money, naturally). Here’s how he spent it.