A Closer Look at the Estate Auction of Stephen Sondheim—Plus Tips on How to Get the Winning Bid

There will be no rest for weary theatre fans this week. Right after Sunday's Tony Awards comes arguably an even bigger day: the June 18 auction of items from the estate of late Broadway legend Stephen Sondheim, hosted by Doyle Auctions.

Playbill got an advance look at the auction house's exhibition of the collection—on display to the public now through June 17 at their New York City location on the Upper East Side. We also speak with some of Doyle's experts about what makes this collection so special—and got some insider tips on how to get that winning bid on the 18th.

This particular set of items is unique in that it represents both memorabilia from the Sweeney Todd and Into the Woods composer-lyricist's many legendary musicals along with lots of personal effects from his two homes, a townhouse in NYC's Turtle Bay and a house in Roxbury, Connecticut. It's no surprise that the stuff related to his musicals will be popular with fans, but Sondheim was so beloved a figure that his furniture and decorations are likely to be popular, too.

"The fan response has been overwhelming," says Peter Costanzo, Doyle's senior vice president and executive director of estate and appraisal services. "We have well over 1,000 bidders set up for the sale, and people are already bidding actively on all elements of the sale, from the furniture to the game collection and the memorabilia."

Some of the furniture is more than just furniture the great man owned, such as a daybed where he famously did much of his writing on, lounging behind his piano in Connecticut. And if you want the full writing experience, you'll also be able to bid on several boxes of vintage Blackwing pencils, Sondheim's favorite.

Items from Doyle's "The Collection of Stephen Sondheim" Auction Vi Dang

And then there's his extensive game collection. He loved to talk about his love of puzzles and games, and particularly how he viewed his lyric writing as a part of that love, which makes the collection even more poignant for Sondheim fans.

"He really fell in love with games and puzzles when he was a kid, spending time with Oscar Hammerstein," shares Doyle cataloguer Noah Goldrach, their resident expert on Sondheim's game collection. Sondheim famously spent much of his youth in Bucks County, Pennsylvania, where his neighbor turned out to be Oscar Hammerstein II, the writer of such musicals as Show Boat, Oklahoma!, and South Pacific. "He would play croquet and chess [there], and he started solving crosswords there too," says Goldrach. "And then as an adult there are all these stories about his famous game nights where he would do these elaborate murder mystery parties."

Those infamous parties inspired friends to start gifting him antique game boards, which Sondheim soon started collecting himself. From playing cards, game boards, puzzles—some as much as 350 years old!—Sondheim collected it all, and had much of it framed for display in his Turtle Bay townhouse.

The collection even includes some promotional puzzles made for the 1973 murder mystery film The Last of Sheila, which Sondheim co-wrote (the rare non-musical project) with Psycho star Anthony Perkins. The film, and Sondheim's love of puzzles, would partially inspire the 2022 film Glass Onion: A Knives Out Mystery, so much so that it featured a posthumous cameo appearance from Sondheim himself. "We have two sets of the puzzle," Goldrach says. "He asked the studio to send him two so that he could open one and make the puzzles while keeping the other pristine. Those were up on a shelf in his house in Roxbury."

One item that caught attention from a lot of theatre fans when this auction's catalogue went live online was a game that Sondheim himself made, a sort of Monopoly for Broadway producers. Bad news theatre fans—this one has been removed from the auction.

But Goldrach got to inspect it pretty closely and hopes we might all get to play it one day. "There were a number of cards that you would place over Broadway theatres, all with different rental costs," he says of the game. "Different plays would be on the cards. They had really funny names, and different operating costs as well. You needed backer cards, and there were reviews. You could actually pay to swap out a bad review for a more favorable one. It was quite elaborate, and apparently Hal Prince was the best at it." Go figure—the 21-time Tony-winning producer and director knew a thing or two about Broadway success!

A handmade ceramic chess set with pieces based on characters from Sondheim musicals Vi Dang

As for the show memorabilia, there's so much to see, from autographed posters to manuscripts, musical manuscripts, scripts, and much, much more—and truly covering his entire career. One of Costanzo's favorite items actually dates from the literal beginning of what would become a legendary songwriting career. "We're so happy to have the first check that Mr. Sondheim received for a published song in 1948," Costanzo shares proudly. "He was at Williams College, and a song got published from a musical he wrote and got on there called Phinney's Rainbow. He earned the grand sum of 74 cents for that." (The satirical musical's title was a play on the then-current Broadway hit Finian's Rainbow, and also made reference to the school's president James Phinney Baxter III.)

You can also find meticulously detailed figurines made based on the original logo to Sweeney Todd, show jackets, a special leather-bound edition of the published Gypsy vocal score, and so much more. There's even items where his love of games and musical theatre intertwine, such as a custom ceramic chessboard with pieces representing characters from his musicals.

Now, if you want to get in on the bidding come June 18, Costanzo says to be ready for stiff competition. "Don't be surprised if the [price] estimates prove to be quite conservative," he says. Having a collection like this from such a prominent figure is pretty unusual—Costanzo calls it a "once-in-a-lifetime opportunity for fans and collectors," and he's absolutely right.

Constanzo heavily suggests coming to Doyle's showroom in NYC, where much of the collection is on display. Particularly if you're interested in snagging some of Sondheim's furniture, seeing it in person may be vital to know if you have somewhere to actually put it.

But that doesn't mean you have to be in New York to participate on June 18. "We are expecting a good-sized crowd here on the day of the sale," says Constanzo, "but we also accept bids over the internet. You can leave bids that we place on your behalf, and you can also bid over the phone."

For more details on the upcoming auction, visit Doyle.com.