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Comedian Gilbert Gottfried had one of the most recognizable voices in the world. With an expansive history in acting, he breathed ear-splitting life into a multitude of iconic characters. However, even hardcore fans might not have known about one of his more obscure roles unless they’re familiar with old word processing software. Let’s take a look back at one of the oddest gigs of a dearly departed talent.

One of his more obscure roles was as the Microsoft Word paperclip, Clippy

In 1990, Microsoft released its original suite of computer applications known as Microsoft Office. It certainly revolutionized the industry, but not without faults. For starters, it could be difficult to figure out how things worked unless you took the time to get familiar with the program. Clearly, it needed some help to become more user-friendly.

In the Windows 97 update, the company made a number of good updates to their Office programs. For Word, the word processor, they introduced a character known as Clippit. Nicknamed Clippy, he was a paperclip mascot that hung out in the corner of your screen, offering suggestions on what to do as you typed.

This infuriated users. Despite their best intentions, Microsoft’s programmers had created an extremely annoying mascot character. Rather than help users understand Word, he became known as “that weird thing that gives unhelpful suggestions.” It wasn’t a good look.

With the introduction of Windows XP in 2001, the company began to phase out Clippy. To promote this, they created a series of Flash videos claiming to have “fired” Clippy because XP was easy enough to use that he was no longer needed. For these ads, they needed someone to play the infamous helper, and who better to do that than the most annoying man in showbiz?

AV Club recapped some of this ad campaign. In addition to the videos, Gottfried also voiced the character at the XP launch event, lamenting his loss of work while introducing the new system.

Clippy may be gone, but he and his voice actor live on in fans’ memories

As much as people hated Clippy while he was there, it was still a shock when Microsoft finally got rid of him. Despite being more of a hindrance than a help most of the time, the character was strangely endearing. Even today, you’ll find people who might have once lambasted him calling for his return. Microsoft itself still makes subtle references to him from time to time, too.

Similarly, Gottfried himself is fondly remembered by fans and friends across the world. Despite being characterized by his shouting, those who met him can speak to his kindness and talent.

Gottfried’s comedy and acting career was based around his voice

Gilbert Gottfried smiling
Gilbert Gottfried | Noam Galai/Getty Images

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Even if you’ve never seen his face, you know Gottfried’s voice. His shrill, shrieking tones have been the basis for his comedy routine since he started. Debuting on The Howard Stern Show, he continued to make numerous appearances on radio, film, and television for years to come.

For many, though, Gottfried’s voice acting is what they remember him by the most. A quick glance at his IMDb will show you just how many characters he had under his belt. Undoubtedly, his most famous role was as the parrot Iago in Aladdin. He turned what could have been a forgettable animal sidekick into a major comedic force, reprising the character for both sequel films, the television series, and even the first Kingdom Hearts game.

Beyond that, though, he also played a number of other characters. In particular, he gave a truly unforgettable performance as the fifth-dimensional imp Mister Mxyzptlk in Superman: The Animated Series, as well as some hilarious parody performances as Jerry Seinfeld and Patrick Swayze in the short-lived Clerks cartoon.