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The Time Freddy Krueger Became a Nightmare for Will Smith

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Fans of Will Smith’s music career may think they’ve heard every album and seen every music video from the actor’s days as one half of the hip-hop duo DJ Jazzy Jeff & the Fresh Prince. Thanks to one ill-timed and poorly conceived effort, however, there’s one performance that aired only a handful of times before being permanently pulled. It has never resurfaced on compilations, on MTV, or even on YouTube. And the fault lies solely with Freddy Krueger, who used something even more dangerous than his razor-fingered glove: a small army of lawyers.

A promotional image of Robert Englund as Freddy Krueger
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Back in early 1988, Smith and his musical partner Jazzy Jeff (a.k.a. Jeffrey Allen Townes) released their second album, He’s the DJ, I’m the Rapper. It would eventually go platinum, selling 2.5 million copies through 1989 and spinning off the duo’s most successful single, “Parents Just Don’t Understand.”

In late 1987, Townes composed another single, “Nightmare on My Street,” that played with the premise established by the A Nightmare on Elm Street series. In the song, Smith’s dreams are haunted by a scarred bogeyman named “Fred”; a voice modulator mimics the raspy delivery of actor Robert Englund, who portrayed slasher movie icon Freddy Krueger in the Nightmare on Elm Street films. After his run-in, Smith tries calling Jeff to warn him of the threat but it was too late: The killer has gotten to his partner.

Zomba, the parent company behind the album's label, decided the song might be of interest to New Line Cinema, the studio behind the Nightmare film franchise. With the fourth installment, A Nightmare on Elm Street 4: The Dream Master, due to hit theaters in August 1988, Zomba executive Barry Weiss approached New Line with the possibility of collaborating and forwarded a tape of the song.

Weiss’s timing was spot-on. New Line had recently conducted research that indicated that 40 percent of A Nightmare of Elm Street's audience was black, and they felt that tying Krueger into the burgeoning rap and hip-hop industry would help cement his appeal to the demographic. But New Line and Weiss couldn’t come to a financial agreement. Instead, the studio went with The Fat Boys and granted permission for the song “Are You Ready for Freddy?” The video, complete with an appearance by Englund (in character), was released just a few months prior to A Nightmare on Elm Street 4 to raise awareness of the sequel.

Although New Line found their collaborators, Zomba didn’t appear willing to give up on the idea of a Freddy takeoff. “Nightmare on My Street” remained on the album, and Smith and Townes recorded a video intended for distribution on MTV. In it, Smith is stalked by a Freddy-like character who appears in a trench coat and has a wrinkled face. Smith’s lyrics make overt reference to a Krueger-esque appearance. (Fred is “burnt like a weenie.”) The eerie house Smith calls home even bears a passing resemblance to the house in the original Nightmare film.

If Zomba thought they could declare the song and video a parody and be safe from legal action, they were mistaken. Almost immediately, New Line's legal team sent a stern letter demanding the music label recall all copies of the song. When that didn't happen, the studio next sought a preliminary injunction to prevent “Nightmare on My Street” from being aired on MTV or elsewhere, citing copyright infringement and a concern that the video would detract from their collaboration with The Fat Boys.

"We own both a character, Freddy Krueger, and the theme music from Nightmare on Elm Street, both of which are protected under the copyright laws," Seth Willenson, New Line's senior vice president of telecommunications, told the Los Angeles Times in August 1988. “By using Freddy in the Jazzy Jeff song, they've infringed our copyright. We're protecting our rights the same way that George Lucas does, because as far as we're concerned, Freddy Krueger is the Star Wars of New Line Cinema."

Weeks before the release of the film, a judge in New York’s United States District Court would have to decide whether Zomba was entitled to a fair use exemption over a fictional child murderer.

Will Smith appears at the Grammy Awards
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To Zomba’s dismay, judge Robert Ward didn’t buy their argument that “Nightmare on My Street” was nothing more than a Weird Al-style satire. Screening the entire first installment of the film series and the music video, Ward noted that the latter drew considerable influence in tone, mood, and characteristics from the feature. Fred’s voice was scratchy like Englund’s; his glove, though it featured phonograph needles instead of razors, was obviously meant to invoke Krueger’s weapon of choice. Where Zomba saw parody, Ward saw little more than a derivative work of a copyrighted property.

“It is in this month that many individuals will make their decision whether Nightmare IV is a film that they are interested in viewing,” wrote Ward in his decision. “Thus, the telecast of the lower quality DJ Jazzy Jeff video with the somewhat silly and less frightening Freddy could dissuade an unspecified number of individuals from seeing the film.” The injunction was granted, with a full hearing to be held at a later date.

That didn’t happen—both parties settled out of court. While the song remained on the record, it began to ship with a disclaimer that it wasn’t associated with New Line; the video, which had aired only briefly on MTV, was pulled, and the court ordered that all copies be destroyed. Whether or not that happened is hard to substantiate, but if the video is lurking in storage somewhere, it has never been excavated. “Nightmare on My Street” has never resurfaced.

If Smith and Townes were bothered by the outcome, they didn’t voice it publicly. Smith even dressed up as Krueger in a 1990 episode of his sitcom, The Fresh Prince of Bel-Air. But there is one additional bit of film trivia to come out of the case: In seeking to resolve the issue, New Line offered DJ Jazzy Jeff and the Fresh Prince a two-film option. If they accepted the roles, their salaries would be deducted from the settlement payout. One of those projects was 1990’s House Party, which the two declined. The roles eventually went to Kid ‘n Play.

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10 Things We Learned From Vanilla Ice's 1991 Autobiography, Ice by Ice
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Vanilla Ice turns 50 on October 31, which will either make you feel very old or compelled to ask a nearby senior who Vanilla Ice is. The hip-hop artist was best known for To the Extreme, his 1990 album that sold 7 million copies, and its breakout single, “Ice, Ice Baby.” He also had a notable turn as himself in 1991’s Teenage Mutant Ninja Turtles II: The Secret of the Ooze before attempting to reinvigorate his career as a Rasta-infused rapper with dreadlocks after his initial novelty wore off.

Before that happened, Ice (a.k.a. Robert Van Winkle) penned Ice by Ice, a 1991 “autobiography” that has no co-author byline but was probably written by a man named Randi Reisfeld, who is thanked by the rapper in the foreword for “putting my thoughts together.” At an economical 164 pages, it’s essential reading for anyone who wanted to know the name of Ice's signature hairstyle (“the beak”) or how women can grab his attention ("dressing super-sexy”). Here are 10 things we learned about the Iceman in this revealing paperback cash grab.

1. HE CUT HIS OWN HAIR.

Even at the height of his fame, Vanilla Ice wouldn’t trust just anyone to get near his trademark pompadour that he dubbed “the beak,” with lines shaved into the sides and a light stripe whooshing through the front. To maintain the look, Ice preferred a DIY approach. “I sit where there’s a mirror behind me and hold another mirror in front of me,” he writes. “That way I can see my whole head.”

Ice was so demanding of his follicles than anything less than perfection would be met with self-banishment. “I don’t like to be photographed unless my hair is perfect—that’s why you’ll see pictures of me in baseball caps a lot.”

2. HE DOESN’T CRY.

“I don’t cry and I don’t know why,” Ice explains. Even when he shattered his ankle as a teenager in a motorcycle accident, Ice didn’t get weepy. The only time he confesses to feeling even a passing sensation of tears is when he was handed plaques for having a platinum record. “My eyes got watery … it’s as close to crying as I’ve ever come.”

3. HE GOT STABBED IN THE BUTT AND LOST FOUR PINTS OF BLOOD.

Vanilla Ice in a Miami Football T
Scott Harrison/Getty Images

As Ice’s popularity grew, much was made of his claims that he grew up in rough parts of Miami and Dallas, where he joined a street gang after his stepfather relocated his family for a job opportunity. Some observers accused him of embellishing his background in order to appear more like a hardcore street urchin. Ice bemoans the fact that he’s felt compelled to pull down his pants to show off the scar on his butt from a knife attack at age 18. According to the rapper, a street fight turned ugly when an attacker pulled a knife and sliced open his thigh and buttocks, requiring an extended hospital stay after he lost four pints of blood. “What they did was put this thing that looked like a Q-tip with alcohol on it down inside my leg to plug up the artery,” he writes. (He didn’t cry, though.)

4. HE WORE MISMATCHED SNEAKERS TO SCHOOL.

Growing up, Ice bounced from school to school, admitting he wasn’t very interested in formal education and jarred by having to be the new kid on a regular basis. To offset that sense of isolation, he began showing up in increasingly outlandish outfits, including wearing mismatched shoes. “I’d wear a boot on one foot and a tennis shoe on the other,” he writes, “wear blue jeans with one leg long, the other leg cut off, stuff like that.”

5. IF HE HAD A PROBLEM, HE REALLY WOULD SOLVE IT.

Ice maintains that he was never comfortable sharing his feelings with others. His mother, who was single until marrying his stepfather when Ice was eight years old, tried to put him into therapy to address his troublemaking ways at school; Ice refused to talk. “I never needed to talk to anyone to solve my problems,” he writes. “A lot of people need someone to talk to, but I’ve never been able to open up and do that. Never could, never will. That’s just the way I am. And that’s just exactly where the ‘Ice, Ice Baby’ hook came from—‘If there was a problem, yo, I’ll solve it.’”

6. HE WOULD SOMETIMES USE DIRTY WORDS.

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Engaging in rap battles growing up, Ice would occasionally deploy some profanity—not because he necessarily wanted to, but because his competitors had started it and he needed to keep up. “The thing is, I wouldn’t do it unless some other rapper started cursing and dissin’ me and the crowd started liking it,” he writes. "'Cause if the crowd starts liking the cursing part, that means to win you’re going to have to curse back at them.” Ice maintains in the book that his raps were clean on his records because “I don’t need to put in dirty words to express myself.”

7. HE WAS ORIGINALLY KNOWN AS VANILLA M.C.

Ice got his start performing at City Lights, a dance club in Dallas owned by future manager Tommy Quon. With “Robert Van Winkle” not having a ton of appeal on a marquee, Ice decided to take the nickname given to him as a teenager when he was beatboxing and rapping in his neighborhood (“Vanilla M.C.”). But Quon pointed out that there were already a lot of “MCs” in the music business, including M.C. Hammer and Young M.C. “You know, your raps, your rhythms are really smooth, smooth as Ice, in fact,” Quon told him. Writing that “it sounded okay to me,” Vanilla M.C. became Vanilla Ice.

8. HE WAS DRAWN TO WOMEN FOR THEIR LOOKS.

Not one to sanitize his image for the masses, Ice admits that his primary concern when dealing with the opposite sex is whether he finds them attractive or not. “My first impression of a girl, whether I’m going to be drawn to her or not, is based on her looks. I know it’s not fair, but then I see what her personality is like.”

Once Ice establishes a woman could engage him intellectually while still “dressing super-sexy,” he enjoys entertaining them at fine dining establishments. But not too fine. “I like candlelit romantic restaurants, but not those where the menu is so fancy that I don’t know what I’m ordering.”

9. HE GOT AN OFFER TO APPEAR IN A NIGHTMARE ON ELM STREET SEQUEL.

Vanilla Ice and Kristin Minter star in 'Cool as Ice' (1991).
Universal Home Video

Ice’s career could have gone in multiple directions following the success of To the Extreme. He filmed a cameo in a Teenage Mutant Ninja Turtles sequel and had his own starring vehicle in 1991’s Cool as Ice. In between those projects, Ice was offered a small role in a Nightmare on Elm Street sequel, presumably to be murdered by Freddy Krueger, “but I didn’t have room in my schedule to take time off for it.” 

10. HE WAS STALKED BY A SATANIST.

We’re cheating slightly, since Ice doesn’t disclose this fact in his book, but it’s still worth noting. At height of Ice mania in the 1990s, the rapper told Rolling Stone that a woman began following him around in an attempt to convert him to Satanism. Ice first noticed the woman at Wembley Stadium when she flashed him in a trench coat. (See: number 8.) Later, the same woman followed him to Japan and left a book under his hotel door: a Satanic Bible, with a personal message to join the flock. Why? Because his birthday falls on Halloween.

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The Tragic Life of Clippy, the World's Most Hated Virtual Assistant
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Microsoft

When a large company stumbles, it’s major news. Coca-Cola infamously angered millions of soda drinkers when it tinkered with its recipe to produce New Coke in 1985. Netflix may now be the country’s biggest single source of entertainment, but it wasn’t long ago they tried to spin off their DVD and streaming services into separate entities, confusing millions of otherwise satisfied consumers.

Stationed somewhere in between those gaffes sits Clippy, the unofficial name for the bouncing, sentient paper clip introduced by Microsoft in 1996 in a bid to help people hone their word processing skills. When Microsoft Office software users began writing a letter by typing “Dear,” for example, out would pop Clippy with an unsolicited offer to help.

The first time this happened, users may have been amused. But as they grew more proficient, Clippy would redouble his efforts to interrupt, his roving eyes scanning documents in what felt like a gross invasion of privacy. In no time at all, he would be the subject of scorn and ridicule, an ever-present voyeur into your home computer navigation.

In order for Microsoft to continue to flourish, Clippy would have to die.

A screen shot featuring Clippy
The Science Elf, YouTube

In the 1990s, Microsoft had already revolutionized personal computing with its Windows interface. Taking navigation out of its sterile DOS command prompts and making it feel more like the welcoming layout of Apple's Macintosh line, Windows helped facilitate the PC boom.

The company wanted to take it one step further with Bob, an operating system programmed to resemble the rooms of a house. Going to the “checkbook” on the desk, for example, would open financial software. Released in 1995, the virtual domain never took off, with users and industry observers declaring it so purposely cute that it was nauseating. (Even worse, the hated typeface Comic Sans was created for use in Bob, perpetuating a cycle of user cruelty.)

Although Microsoft quickly abandoned Bob, it seemed stuck on one of the characters that populated the OS: Clippit, an energetic paper clip that injected itself into tasks to see if it could make the experience easier on users. According to Clippit illustrator Kevan Atteberry, Microsoft had developed over 250 characters for such a purpose: Clippit, which users later re-named “Clippy,” won out, and the company decided to keep him around for the 1996 release of its word processing software.

Despite Microsoft harnessing the knowledge of social psychologists from Stanford to develop these software assistants, there were early signs Clippy was destined to annoy users. Focus groups exposed to the character made frequent references to his “leering” eyes, which female product testers found particularly unsettling. (Though he lacked any genitalia, Clippy was labeled male by Microsoft.)

Failing to heed their criticism, Microsoft inserted Clippy into the version of Office released in 1996. Users opening a blank document were greeted by a jovial paper clip that offered advice on everything from spelling to saving files. Even if keyboard shortcuts and other operating commands were mastered, Clippy materialized from the ether, repeating himself until they could figure out how to shut him up for good. (For Office 1997 users, that meant manually changing his program folder name from "Actors" to "NoActors.")

Although Clippy received the brunt of criticism, he wasn’t the only Office mascot available to distract and annoy. The Genius was an Einstein-esque icon; Power Pup was a dog that could help you retrieve information. But Clippy was the pre-set helper, and his wiggling eyebrows and contorted paper clip frame burrowed into Windows users' psyches.

Clippy meets his maker
Stan Honda/Getty Images

Microsoft was not insulated from the Clippy criticism. Writing of his time working for the company, James Fallows reported for The Atlantic in 2008 that the excitable little stationery accessory was bemoaned by employees. Yet Clippy remained, getting a minor makeover in Office 2000 before being automatically turned off in 2002. (Microsoft poked fun at the user enmity, announcing the character was out of work and creating a game that allowed players to zap Clippy with a staple gun.)

Why the allegiance? Fallows said it was in part related to Clippy’s origin as a resident of the failed Bob operating system. That project was spearheaded by Melinda French, who later became Melinda French Gates, wife of Microsoft founder Bill Gates. While Fallows is quick to point out that it wasn’t the sole reason Clippy remained an uninvited guest, no one was particularly enthusiastic about getting rid of him, either.

Clippy eventually met his end in 2007, when the latest version of Office shipped without his grating interjections. Distanced from the pain of actually having to deal with him, a number of Clippy’s critics began to produce damning fan art, from Clippy being a general nuisance to engaging in lewd acts. In 2015, author Leonard Delaney self-published Conquered by Clippy, a 16-page erotic short story that was either a meditation on how technology is seducing us or just a weird story about a paper clip copulating with a human. (Delaney also penned Taken by Tetris Blocks.)

Clippy’s final bow—for now, at least—came earlier in 2017, when an anonymous programmer offered a Chrome extension that allows Clippy to pop up virtually everywhere you go. Like the original, he’s basically useless.

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