The eclectic art collection of the late comedian and actor Robin Williams and his former wife Masha will go under the hammer at Sotheby’s New York on October 4.

The collection includes a large array of weird and wonderful items, including fine art, film collectibles, watches, design, and sports memorabilia. Ahead of the auction, Sotheby’s estimates that the sale will gross between $3.3 million and $4.7 million. The actor’s family has chosen to distribute the proceeds to a number of charities—including the Wounded Warrior Project, the Challenged Athletes Foundation, the Christopher and Dana Reeve collection—and towards the establishment of a permanent Robin Williams Scholarship Fund at the Juilliard School in New York.

Ahead of the sale, we picked some of the highlights and strange tidbits that illustrate the actor’s personality, accomplishments, and famous sense of humor.

1. Robin Williams’s Golden Globe Awards (est. $15,000–20,000)

Golden Globe awarded to Robin Williams for his performance in Good Morning Vietnam (1987). Photo courtesy of Sotheby’s.

The sale includes more than 40 awards and certificates from the couple’s television and movie careers, but none is more prestigious than Williams’s Golden Globe Awards for his roles in Mork and Mindy, Good Morning Vietnam, The Fisher King, and Mrs. Doubtfire, some of the crowning achievements of Williams’s acting career. (The family elected to keep his Academy Award, which he won for Best Supporting Actor for his role in the 1998 hit movie Good Will Hunting.)

2. Niki de Saint-Phalle’s Le poète et sa muse (est. $350,000–450,000)

Niki de Saint-Phalle, Le poète et sa muse. Photo courtesy of Sotheby’s.

Most of the Williams art collection focused on large-scale outdoor sculpture, which the couple displayed on the grounds of their Napa Valley home. One of Robin’s favorite works was Niki de Saint-Phalle’s Le poète et sa muse, which he gave to Masha as a gift. When the artist, who was staying nearby, found out that the actor bought the work, she anonymously left a decorated postcard in his mailbox signed “from a fan.”

3. Banksy’s Happy Choppers (2006) (est. $400,000–600,000)

Banksy, Happy Choppers (2006). Photo courtesy of Sotheby’s.

The Williamses also liked to collect street art—they bought works by Banksy, Shepard Fairey, Invader, Mr. Brainwash. The centerpiece of their street art collection is undoubtedly Banksy’s Happy Choppers (2006), a rare large-scale original piece by the elusive British painter.

4. Franck Muller; White Gold Tonneau-Form Minute Repeating Tourbillon Wristwatch (1988) (est. $25,000–30,000)

Franck Muller, White Gold Tonneau-Form Tourbillon Wristwatch (1988). Photo courtesy of Sotheby’s.

The comedian was a discerning high-end wristwatch collector, accumulating dozens of collectible timepieces, some of which he bought and some of which were given to him as gifts by his wife and others. At the upcoming sale, Sotheby’s is offering more than 40 armbands from his personal collection, led by a Franck Muller wristwatch in white gold.

5. Judy Kensley McKie’s “Monkey” Armchairs (1994) (est. $20,000–30,000)

Judy Kensley McKie, “Monkey” armchair. Photo courtesy of Sotheby’s.

Designer Judy Kensley McKie’s playful wooden armchair incorporates two monkeys, illustrating how the comedian’s sense of humor pervaded his whole life, right down to his taste in furniture. Sotheby’s is offering a group of five examples of these whimsical pieces from the actor’s design collection.

6. Everlast Boxing Gloves signed by Muhammad Ali (est. $1,000–2,000)

Muhammad Ali’s signed boxing gloves. Photo courtesy of Sotheby’s.

A major sports fan, Williams collected a range of memorabilia, including lots of exclusive signed pieces, including an autographed baseball signed by Yogi Berra and a Cleveland Cavaliers jersey signed by superstar Lebron James. But perhaps no item is more impressive than a pair of boxing gloves bearing the signature of the legendary Muhammad Ali. The gloves were presented to the actor in 2006 when he was honored with the Muhammad Ali Humanitarian Award at the boxer’s annual Celebrity Fight Night.

7. First Edition of Samuel Beckett’s Waiting for Godot (est. $1,500–2,500)

Samuel Beckett’s Waiting for Godot. Photo courtesy of Sotheby’s.

Williams’s extensive collecting habit extended to rare books, including three first editions of one of the most influential plays of the 20th century, Beckett’s Waiting for Godot. Demonstrating the actor’s breadth and versatility, Williams performed in a production of the play at New York’s Lincoln Center in 1988, directed by Mike Nichols and also starring fellow comedian Steve Martin and acclaimed actor F. Murray Abraham.