Buddy Holly's Motorcycle, Willie Nelson's Braids Part of Giant Waylon Jennings Auction

Waylon Jennings sure collected a lot of strange items during his life. Now, several hundred of them are going on auction at the Musical Instrument Museum, including a motorcycle once owned by Buddy Holly, a pair of Hank Williams' boots, Willie Nelson's braids, and a whole lot of clothing, jewelery, and other memorabilia.

The late Jennings was one of the Valley's all-time most famous residents, but let's back up a minute. Jennings is one of the most important and influential country singers of all time, a decorated and venerated member of the outlaw country movement, and the singer on five platinum records and 15 songs that topped the U.S. country charts. And he did almost all of it all after moving to Arizona.

Check out the highlights from the auction below.

Lot 235 - Buddy Holly and Waylon Jennings' 1958 Ariel Cyclone Motorcycle

Famously, Waylon Jennings was almost part of the Day the Music Died. The story goes that Jennings almost boarded the fateful plane that carried Buddy Holly, Richie Valens, and the Big Bopper (J.P. Richardson) to their doom in 1959. He was on tour with Holly as part of his backing band, and Holly chartered a plane and invited Jennings to join. Jennings, however, gave up his seat to Richardson, who was battling the flu and thought the plane ride would be more healthful. Jennings instead boarded the band's tour bus.

Holly and Jennings had a famous exchange before the plane took off -- Holly teased Jennings, saying that he hoped the bus crashed, and Jennings said he hoped the plane crashed.

After Holly's death, the bike bounced around between a few owners before a few members of the Crickets banded together and bought the bike as a gift for Jennings. The bike has very little wear on it and, besides the tires, contains all original parts. The starting bid for the Cyclone is $50,000, but auctioneer Arlan Ettinger thinks that it's not a question of if the bike will sell for hundreds of thousands of dollars, but how many.

Lot 249 - Willie Nelson's Trademark Braids, 1983

The story behind these braids is that Nelson and Jennings, fast friends, had a bet going on who could give up drugs the quickest. Jennings lost, and as a result, chopped off his braids and had his wife present them to Jennings at a party. Estimated value: $50,000 to $60,000.

Lot 41 - Photograph of Waylon Jennings and Johnny Cash Rollerskating

This 11-inch-by-14-inch photo of two badass outlaw country singers lacing up their skates is estimated at $400-$600 in value.

Lot 89 - The Highwayman Goes Gold, 1986

This is Jennings' gold record for The Highwayman, the self-titled debut of the supergroup comprising Kris Kristofferson, Johnny Cash, Jennings, and Willie Nelson.Estimated value: $3,000-$4,000.

Lot 286 - Letter from John Lennon to Waylon

We're not sure the context of this letter. All we know for sure is that what is most striking is John Lennon's use of a smiley face to sign his letter. Was the musical pioneer also a linguistic one? Did he somehow, in an acid trip with Yoko, perhaps, anticipate the use of emoticons decades after his death?

Jennings' plaque celebrating 5 million copies of Waylon's Greatest Hits sold. No estimate available.

Lot 172 - Waylon Jennings' Passport

Jennings used this while touring the world with The Highwaymen, and his passport includes stamps from New Zealand, Singapore, Thailand, and Australia. Estimated values: $10,000-$15,000. Yikes.

Lot 120 - C. 1946 Martin D28 Herringbone Guitar

This is Jennings' personal guitar, one he reportedly used for songwriting and for playing at home. It features a spruce top with a herringbone edge, mahogany neck, and an ebony fingerboard and bridge. The back and sides are Brazilian rosewood. It's a gorgeous guitar, with an estimated value of a nice sports car. The guitar might sell in the range of $30,000 to $40,000.

Lot 132 - Waylon Jennings Unidentified Guitar

There's no label on this guitar, but the unusual mosaic design makes it stand out. Its estimated value is $1,000 to $1,500.

Lot 136 - Dobro Resonator Guitar With Pickup

Little Jimmy Dickens, pint-sized singer and oldest living member of the Show that Made Country Music Famous, the Grand Ole Opry, gave this guitar to Jennings, as evidenced by the subtle appearance of Dickens' name on the neck. This guitar is in excellent condition, according to the auctioneers, and is estimated at $6,000 to $8,000 in value.

Lot 137 - 1996 Fender Custom Shop Waylon Jennings Telecaster

The sixth Waylon Jennings signature guitar Fender made in the '90s after teaming up with Jennings to replicate his '63 Telecaster. This has light signs of use, and is estimated at $10,000 to $15,000 in value.

Lot 292A - Waylon Jennings' Rolex Submariner Wristwatch

A wristwatch Jennings' wife Jessi Colter gave to him after he remarked that he wished he had a watch big enough to read while on stage. The 18K gold watch features Jennings' and his wife's initials engraved on the back. Estimated value: $30,000 to $50,000.

Lot 418 - Shirt with Fire Print

Proving that even country music legends had questionable fashion sense, you can fan the flames of your love for Jennings with this hideous ensemble. He wore this often while performing. This does not come with the belt picture in the photo, and is estimated to be worth $2,000 to $2,500

While recording The Highwayman, Johnny Cash gave this desk to Jennings. Not one to care about besmirching such a gorgeous piece of cabinetry, Jennings used the insides of the top drawers as a Rolodex, inscribing the numbers of Cash, Nelson, Hank Williams Jr., and others. Chair included. Estimated value is $30,000 to $50,000.

Jennings lived in Scottsdale for many years, and in the '90s, the city's then-mayor Herb Drinkwater presented this to Jennings. Estimated value $1,000 to $1,500.

Lot 239 - Muhammad Ali's Training gloves

Jennings loved boxing, and was a huge fan of Muhammad Ali. When Kris Kristofferson introduced the two in 1978, Jennings and Ali got along great, and Ali gave Jennings the pictured pair of gloves. Estimated value:$10,000 to $15,000.

Lot 283 - Original Contract forming the Country Supergroup The Highwaymen, August 1989

This here is the original contract that formed the supergroup the Highwaymen, which featured Jennings, Kris Kristofferson, Willie Nelson, and Johnny Cash. The group's records went on to sell millions of copies, and this contract contains the signatures of all four. The estimated value of this one is $80,000 to $100,000.

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