October 28, 2012: More than a year after Steve Jobs’ death, the luxury yacht he commissioned is finally shown off for the first time, launched from a shipyard in North Holland.

Called Venus, the distinctive-looking yacht was one of the big personal projects Jobs pursued in his last years. As he told biographer Walter Isaacson, “I have to keep going on it. If I don’t, it’s an admission that I’m about to die.”

Sadly, Jobs never lived to see the finished vessel.

October 27, 1999: Dell Computer overtakes Apple in the educational market, stealing Cupertino’s crown as the top company selling computers to U.S. schools.

Steve Jobs, who is still in the process of rebuilding Apple after its near-collapse in the 1990s, faces heavy criticism for ignoring one of the company’s strongest markets.

October 24, 1988: Three years after leaving Apple, Steve Jobs prepares to launch the NeXT Computer, a machine he hopes will cement his reputation as a tech genius and blow away the machines produced by Cupertino.

The new NeXT Computer receives a wave of positive publicity. Fawning stories show exactly what the 33-year-old Jobs has been working on — and what’s coming next.

October 23, 2001: Apple CEO Steve Jobs introduces the first iPod, a device capable of holding an entire music library in a highly portable package.

The first-generation device boasts a 5GB hard drive capable of storing “1,000 songs in your pocket.” That may not sound too dazzling in a world in which people can stream the massive Apple Music library from their iPhones. But it was a game-changer at the time!

Editor’s note: Today marks the 20th anniversary of the iPod, the humble digital music player that reshaped Apple. To mark the occasion, Cult of Mac updated its illustrated history of the iPod — put together to celebrate the device’s 10th anniversary, and originally published on Oct. 22, 2011.

An Illustrated History of the iPod

The iPod grew out of Steve Jobs’ digital hub strategy. Life was going digital. People were plugging all kinds of devices into their computers: digital cameras, camcorders, MP3 players.

The computer was the central device, the “digital hub,” that could be used to edit photos and movies or manage a large music library. Jobs tasked Apple’s programmers with making software for editing photos, movies and managing digital music. While they were doing this, they discovered that all the early MP3 players were horrible. Jobs asked his top hardware guy, Jon Rubinstein, to see if Apple could do better.

An incredibly rare Apple VideoPad 2 prototype is headed to auction after it was purchased from an Apple engineer back in 1999. It comes with a black leather carrying case that features the Newton logo, and is expected to fetch $12,000.

The VideoPad, which was scrapped by Steve Jobs upon his return to Apple in 1997, was a personal digital assistant (PDA) similar to the Newton that would have allowed users to carry out video calls. But it never made it to market.

October 20, 2009: Apple goes big with its iMac redesign, introducing the first 27-inch all-in-one Mac.

The sleek, sophisticated aluminum unibody design looks so good that the iMac will remain virtually unchanged for years. As with the first Macintosh with a built-in CD-ROM drive, the iMac’s 27-inch display represents a sea change for tech. The big, beautiful screen signals that larger displays need no longer remain the domain of pampered professionals.

As many Apple fans knows, the company’s first products was the Apple-1 personal computer, initially put together in a garage by Steve Wozniak and Steve Jobs in 1976. Now one unit in their early run of 200, known as the “Chaffey College Apple-1” because its first owner taught there, is going up for auction November 9 with a starting bid of $200,000.

October 16, 2003: Six months after opening the iTunes Music Store for Mac owners, Apple expands the service to cover Windows PCs as well.

Apple CEO Steve Jobs later quips that making iTunes available to Windows owners is akin to “giving a glass of ice water to somebody in hell.”