On Monday (1 March) a painting by Sir Winston Churchill that was owned by Hollywood star Angelina Jolie sold for just over £8 million ($11m) at an online Christie's auction in London. The most ever paid for a work by the UK's former prime minister, the painting Tower Of The Koutoubia Mosque features the Atlas Mountains in Marrakech and is the only artwork Churchill created during wartime.

He painted it after the Casablanca Conference of January 1943, where he and US president Franklin Roosevelt planned the actions that led to the defeat of Nazi Germany. After the conference he persuaded Roosevelt to travel 150 miles to Marrakech and watch the sunset on the mountains there. The next day Churchill painted the scene, which he later sent to Roosevelt as a birthday gift. 

It was sold on after Roosevelt's death and in 2011 it was bought by Jolie and her former partner Brad Pitt. Now the painting, which serves as a momento of the UK-US's 'special relationship', has been bought by an unknown buyer. Click or scroll on to see some other record-breaking auctions from the past year. All dollar values in US dollars unless otherwise stated.

It’s not often that a toilet seat cover is keenly snapped up by auction-goers, but this wasn’t just any old bathroom accessory – this belonged to ex-Rolling Stones bassist Bill Wyman. The plush yellow seat cover features the band’s iconic tongue and lips logo and is believed to date back to the Stones’ 1975 American tour. Auctioneers underestimated how much this piece would fetch, and 10 bidders drove the price up to $1,152 (£887), which was twice the original estimate, at an auction in September.

Popular Japanese comic and cartooning style Manga has fans all over the world – fans willing to pay big bucks for the most popular pieces. This acrylic artwork from Knights of the Zodiac: Saint Seiya was produced between 1987 and 1988, and its good condition and popularity led to it selling for an astonishing $48,387 (£37.2k) at an auction last summer, making it the most expensive Manga animation to be sold last year.

Like many big businesses, Disney has seen parts of its empire struggle due to coronavirus, but that hasn’t deterred fans who want to own a piece of the magic. In 2020 the priciest piece of Disney memorabilia was this entrance sign, which originally hung outside Don DeFore’s Silver Banjo Barbeque in Frontierland at Disneyland California. The restaurant was a popular part of the Disney theme park until 1961, when it was closed to allow for the expansion of the nearby Aunt Jemima’s Kitchen. Actor Don DeFore, whose name adorned the restaurant, displayed the sign in his home for many years following the restaurant’s closure, hiking up the price of this extraordinary piece to $56,250 (£43.3k) at the August auction.

This baseball button became the most expensive button ever sold when it was auctioned off for $62,980 (£48.6k) in September last year. It was the only existing 1916 World Championship Series button known to experts and, at six inches in diameter, was the largest made at its time of production. The celluloid button was the main attraction among a collection of pop culture memorabilia at Live Auctioneers, which altogether fetched $2.1 million (£1.6m).

Vintage alcohol can make a mint, and last July a rare bottle from 1951 became the most expensive bottle of Australian wine ever sold. Fewer than 20 bottles of the Penfolds 51 Bin 1 Grange are in circulation, which justified the incredible price of AU$103,555, which equates to $74,000 (£57k) – or roughly $14,664 (£11.3k) per glass. In 2019 an entire set of Penfolds vintages spanning 1951 to 2015 fetched AU$372,800 ($267k/£206k), which was another record-breaking sum.

Gamers go wild for vintage consoles and cartridges and in July last year a sealed 1985 Super Mario Bros game smashed records when it sold for $114,000 (£87.8k), making it the most expensive video game ever sold. This was a particularly special edition as it had never been played and also still had the original hangtab attached.

A bottle of Gautier from 1762 broke the record for the most expensive cognac ever sold in May 2020 when bidding closed at Sotheby’s auction house at £118,580 ($154k). The alcohol was bottled around the 1840s and, although there are clear signs of its age, collectors weren't deterred from bidding into the high figures for this rare example. The Gautier was sold in the same auction as other bottles of the world’s oldest cognacs, with the collection fetching $1.8 million (£1.4m) in total.

There’s a big market for restored motorcycles, but incredibly this spotless 109-year-old bike has never had any work done to it – it’s just been kept in remarkable condition. This 1911 Arrow Four was one of the highly coveted vehicles produced by Pierce in the early 1900s, and the company was the motorcycle equivalent of Rolls-Royce in its day. Mecum Auctions described the vehicle as “probably the best example” of its kind in the world, hence its big price tag of $225,500 (£173.7k) when it went under the hammer in July last year.

Whether they’re based on kids’ TV shows or the best baseball players in the world, cards are highly collectable. This mint-condition Pokémon card was especially desirable thanks to its rarity – it could only be obtained through a Japanese comic book contest in 1998, and of the 39 originally released only 10 are thought to still be around. This ‘Pikachu Illustrator’ has become the most expensive Pokémon card ever sold, with a collector picking it up for $236,831 (£182.5k) in July last year. It has taken the title off an example of the very same card, which sold for $190,000 (£146.5k) in 2019.

In 1962 the late Sean Connery was the first actor to bring Ian Fleming’s James Bond to life in the first 007 movie Dr. No. And so when a Walther PP handgun used by Connery during the film recently went up for sale in Beverly Hills in December it was expected to sell for a high price. In fact, the pistol exceeded all expectations when it sold for a record $256,000 (£194k). The collector’s value of the prop was likely inflated after Connery passed away at the end of October 2020, aged 90. 

In July last year, a Hermès handbag became the most expensive ever auctioned when it sold through Christie’s for £230,000 ($297k). The designer bag is controversially made of Niloticus crocodile skin, native to Africa, and covered in 18k white gold and diamond hardware, including multiple padlocks. The Himalaya Birkin bag was made in 2016 and is the first of its kind to sell at an auction house. While this Hermès piece is the most expensive bag sold in 2020, it's also the most expensive ever sold in the United States, and also claims the title of the highest price ever achieved at an online handbag auction.

While Sony and Nintendo’s collaboration to create the ‘Nintendo Play Station’ was a complete flop, a rare prototype of the failed console hit the record books in March 2020 when it became the most expensive console ever sold. The dual-branded prototype was discovered in an attic in 2015, after many had dismissed its existence as myth, and went on to sell for $300,000 (£231k) through Heritage Auctions.

Believed to be the most expensive pair of glasses ever sold, the eyewear of none other than Indian politician Mahatma Gandhi sold for £260,000 ($340k) through East Bristol Auctions in August last year. Mysteriously the gold-plated spectacles were found in the auction house’s letterbox, having been left there by a man who had received them from his uncle. Gandhi had been known to give his glasses to people in need and to those who had helped him. The glasses sold for more than 17 times the estimate, with the monetary value of the spectacles also reflecting their historical significance. 

Back to the Rolling Stones' Bill Wyman's auction. The musician’s 1969 Fender Mustang bass guitar sold for $384,000 (£297k) in September last year, making it the priciest bass guitar sold at auction. Unsurprisingly the instrument is steeped in history, having been played at Stones concerts and recordings during 1969 and 1970, as well as appearing in the O2 Arena Rock Exhibition in 2010. Wyman’s 1962 Vox AC30 amplifier also broke records at the same auction when it fetched $106,250 (£82k), making it the most expensive amp ever sold.

Every number plate is unique, and the fewer the symbols, the higher the price. In September, a number plate that read ‘J 4’ sold for £300,000 ($389k) in the UK. While each country has its own system, it is thought that the most expensive number plate ever sold simply read “1”, and was purchased by Saeed Abdel Ghaffar Khouri (pictured) in 2007 for $14.2 million (£7.2m).

This Volkswagen Beetle-based buggy became the most expensive ever sold in March 2020 when it fetched $456,000 (£352k) at auction. This little vehicle was a memorable feature of the 1968 movie The Thomas Crown Affair, and was actually incorporated, and partially designed, by the King of Cool himself, Steve McQueen. The actor insisted that the buggy would be a more appropriate fit for his character than the Jeep that was originally scripted. The vehicle is a veritable one-off and, thanks to its world-famous driver, sold for hundreds of thousands of dollars more than 50 years after its big screen debut.

Breeders will pay big sums for premium livestock, and Texel ram Double Diamond, similar to the lamb pictured, was as close to genetically perfect as sheep get. Three breeders came together to win the auction last August, paying a combined sum of £367,500 ($477k) for the animal and making Double Diamond the most expensive sheep ever sold.

There are jewels, both figuratively and literally, aplenty in this round-up, but how about this plastic crown? Renowned rapper The Notorious B.I.G. picked up this trinket for just $6 and signed it, before modelling it in a photoshoot in 1997 where he posed as the King of New York. The star was assassinated just three days later, and the crown has since gained legendary status. That was reflected in its auction price last September when it sold for $594,750 (£458.5k), more than double the estimate.

Basketball legend Michael Jordan has made millions more via his collaborations with Nike than through his actual sporting career, and when a pair of his sneakers go up for sale, auctioneers know to expect big money. Last August, Christie’s sold off nine pairs of the sporting legend’s shoes in celebration of Jordan’s 14-year career with the Chicago Bulls. The bestsellers were the Nike Air Jordan 1 High shoes worn during a 1985 exhibition game, and they sold for a record-breaking $615,000 (£457k).

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Described as the "most important silver dollar ever struck", this example of the so-called 'flowing hair' design coin dates from 1794 and was owned by the late entrepreneur and owner of the Utah Jazz basketball team, Larry H. Miller. One of the most prized US coins, it sold in December for over $1 million (£720k) to legendary American coin collector Steven Contursi, who had actually sold another 1794 silver dollar back in 2010 for a huge $7.85 million (£5.2m). That coin, which subsequently sold for a record-breaking $10 million (£6.7m) in 2013, was put up for sale in October but failed to meet its reserve price – perhaps a sign of these troubled times?

As previously mentioned, Britain’s World War II prime minister took great pleasure in painting, and his artwork has garnered the interest of plenty of collectors. Winston Churchill painted this particular piece, Jug with Bottles, at Chartwell, his home in Kent, England. Included in the image are a bottle of Johnnie Walker Black Label, one of the politician’s favourite whiskies, and what is suspected to be a bottle of brandy, both displayed on a silver tray. Churchill had gifted the painting to US diplomat Averell Harriman in the 1940s, and it was then auctioned in 1997. When it went up for auction again last November, it fetched £938,000 ($1.3m), making it one of the most expensive Churchill pieces ever auctioned, although short of the price of the Marrakech painting that owned by Angelina Jolie.

The priciest comic book auctioned over the past year was a copy of Detective Comics No.27 from 1939. It was the first to feature Batman, and has now taken the title of the most expensive comic featuring that character ever sold at auction, selling for $1.5 million (£1.1m) at a Heritage Auctions sale in November. The copy was unrestored, and its remarkable condition certainly boosted its value. The most expensive comic ever auctioned was an Action Comics copy featuring Superman, which sold for a whopping $3.2 million (£1.9m) in 2014.

In August last year, a Rolex Daytona became the most expensive watch ever sold at an online auction, with a final price of $1.58 million (£1.2m). This ‘John Player Special’ vintage watch – so named because of the livery used by Lotus Formula 1 team cars in the 70s and 80s – is 18-carat yellow gold and is considered one of the most sought-after watches of all time. It is also the priciest wristwatch auction house Sotheby’s has ever sold in the UK. Good watches never come cheap – the most expensive piece currently on the market is the Graff Diamonds Hallucination, featuring a total of 110 carats of diamonds, which costs a staggering $55 million (£42.4m).

Another collectable card, this time of the sporting variety. In September, a rookie (first appearance) card signed by NBA basketball player Giannis Antetokounmpo became the most expensive basketball card ever sold, fetching an impressive $1.81 million (£1.4m) at auction. Before this sale, the top spot had been held for a brief period by the LeBron James rookie card, which sold for $1.8 million (£1.39m) last July.

A rare Mike Trout baseball card, and other record-breaking sales 

Belgian racing pigeons are known for being the best in the business, and in mid-November a record was broken for the most expensive ever sold. The female pigeon, called New Kim, is two years old and sold to an anonymous Chinese bidder for an incredible €1.6 million ($1.9m/£1.4m), smashing the previous record of €1.25 million ($1.5m/£1.1m), which was set by a male pigeon called Armando (pictured) in March 2019. It was a shock sale as female birds are typically thought to be worth less than males because male birds can produce more offspring while female birds only have 10 years of breeding. New Kim had only raced in 2018 and retired early for breeding after being crowned "best young bird". The pricey pigeon was one of 445 of the birds sold by acclaimed pigeon breeder Gaston Van de Wouwer in November, and overall the auction raised more than €6 million ($7.3m/£5.5m).

Airlines have been doing what they can to stay afloat during the coronavirus pandemic, and British Airways decided to sell a selection of its memorabilia as a way to make extra money. Fans of the airline could buy works of art, dinnerware and trolleys that had been installed in its offices and used onboard its aircraft. But the most expensive piece sold was the Bridget Riley painting Cool Edge (pictured), which had taken pride of place in Heathrow Airport’s executive lounge. The piece surpassed estimates when it sold for £1.9 million ($2.5m) in July last year. Riley often fetches high figures for her abstract work, and her most expensive painting, Chant 2, sold for £2.9 million ($3.8m) in 2014. 

The most expensive guitar ever sold belonged to Nirvana frontman Kurt Cobain and wealthy fans pushed the final price up to a jaw-dropping $6 million (£4.6m) when it went under the hammer in June 2020. The instrument gained fame after being played by Cobain during the legendary MTV Unplugged session in 1993, which has been hailed as one of the greatest live music performances of all time. Unusually, the new owner of the multimillion-dollar guitar was happy to be named as Peter Freedman, founder of RØDE Microphones. The Australian entrepreneur plans to exhibit the instrument across the world and donate the proceeds to the performing arts. 

It may not come as a surprise that the most expensive work of printed literature ever sold was written by William Shakespeare. This First Folio was compiled in 1623 by two of Shakespeare’s friends, seven years after he died, and contains 36 of the playwright’s works. Half of the bard’s best-known plays, including Macbeth, Twelfth Night, and Julius Caesar, weren’t actually published within his lifetime, and may have been lost altogether had they not been published by his friends. This manuscript is believed to be one of just six complete copies that are privately owned, and so when it went up for auction in October last year it fetched an astonishing $9.98 million (£7.6m). The last complete First Folio to come up for sale sold for more than $6 million (£4m) in 2001.

The award for the most expensive car sold at auction over the past year goes to the 1934 Bugatti Type 59 Sports, which sold for £9.5 million ($12.3m) through London-based auctioneers Gooding & Company. While it carried a huge price tag, the car was expected to sell for more than £10 million ($13m), and its falling short of the top price may be down to the economic effects of the coronavirus pandemic. The car was a Works Grand Prix car for the 1934 and 1935 seasons, before being converted to a sports car configuration and continuing to race in 1937.

As auction houses continued to operate virtually throughout the pandemic, a bidder smashed the world record for the most expensive jewel ever purchased online last September. A private collector from Japan dialled in to bid $15.7 million (£12.1m) for the 102.39-carat white diamond, which had been cut from an even larger diamond originally unearthed in Victor Mine in Ontario, Canada. The stone was auctioned without a reserve, meaning that it would go to the highest bidder, regardless of its worth or the final sum. The buyer was anonymous, but is said to have purchased the diamond for his youngest daughter, and named it Maiko Star after her. He purchased a gem of similar size and value last year for his eldest daughter, giving each of them a sizeable nest egg.

A Russian diamond broke records at a Sotheby’s auction in November for being the biggest pink diamond ever auctioned. The Spirit of the Rose diamond is rare because it weighs 14.8 carats, while 99% of pink diamonds weigh less than 10 carats. Unsurprisingly the flawless pink-purple stone fetched an incredible price, with an anonymous bidder agreeing to a sale price of $26.6 million (£20.1m). It didn't achieve the title of the most expensive pink diamond ever sold though, which continues to be held by the CTF Pink Star after it sold for a jaw-dropping $71 million (£57m) at a Sotheby's auction in Hong Kong in 2017.

Stan the dinosaur, named after amateur palaeontologist Stan Sacrison who first discovered the skeleton in 1987, became the most expensive dinosaur fossil ever sold when the hammer came down at $31.8 million (£24.5m) at a Christie’s auction in October last year. The estimate was originally $8 million (£6.2m) – just over a quarter of the final sale price. At 13 feet tall and 40 feet in length, the T. rex is nearly fully intact and is made up of 188 bones. Scientists have spent years studying the prehistoric animal’s remains, and the skeleton is believed to be one of the best specimens ever unearthed. 

Now take a look at the world's most expensive things ever sold