The Best Hip-Hop Music Videos of 1999

This article is a collaborative effort, crafted and edited by a team of dedicated professionals.

Contributors: Andranick Tanguiane, Fred Lerdahl,

The best music videos of 1999 brought us a new wave of hip-hop. From Missy Elliott’s iconic “She’s a Bitch” to Jay-Z’s “Hard Knock Life (Ghetto Anthem),” these were the videos that defined the genre.

The Best Hip-Hop Videos of 1999

1999 was a big year for hip-hop. With the release of several classic albums, it was also a big year for music videos. From Missy Elliott’s “She’s a Bitch” to Jay-Z’s “Hard Knock Life (Ghetto Anthem),” there were a lot of great videos to choose from. Let’s take a look at the best of the best.

Missy Elliot – “She’s a Bitch”

Missy Elliot’s “She’s a Bitch” is often considered one of the best hip-hop videos of 1999. The video features Missy Elliot as a super hero, who must save the day from evil. The video is full of action and special effects, and is one of Missy Elliot’s most iconic videos.

Eminem – “My Name Is”

“My Name Is” is the debut single by American rapper Eminem. It was released on February 23, 1999, as the lead single from his major-label debut album The Slim Shady LP (1999). The song was produced by Dr. Dre, with additional production from The 45 King. The song’s subject matter concerns child abuse, drug use, bills and having little money. “My Name Is” became a sleeper hit in the spring of 1999 and helped Eminem’s album reach number two on the Billboard 200 albums chart and go on to be certified quadruple-platinum by the Recording Industry Association of America (RIAA) in 2000.

Dr. Dre – “Still D.R.E.”

Directed by Hype Williams, “Still D.R.E.” finds Dr. Dre doing what he does best — lookingFly AF while posted up in front of some very expensive cars. The track, which features Snoop Dogg, would go on to be one of the most iconic songs in hip-hop history, and the video is a timeless classic.

Jay-Z – “Hard Knock Life (Ghetto Anthem)”

“Hard Knock Life (Ghetto Anthem)” is the third single from American rapper Jay-Z’s third album Vol. 2… Hard Knock Life. It features a pop-influenced version of the song “It’s the Hard Knock Life” from the 1977 musical Annie. The song was produced by The Trackmasters, who sampled Quincy Jones’ version of “It’s the Hard Knock Life” for the track. It was released as a single on September 29, 1998. The song peaked at number fifteen on the US Billboard Hot 100 chart and number five on the US Billboard Hot Rap Songs chart. Outside of the United States, “Hard Knock Life (Ghetto Anthem)” peaked within the top ten of the charts in Denmark, Netherlands and New Zealand; and within the top twenty of both Australia and Canada.

The music video for “Hard Knock Life (Ghetto Anthem)” was directed by Hype Williams and shot in black-and-white. Throughout most of it, Jay-Z is seen rapping in variousア ステージ settings surrounded by a mob of people, who are constantly gesturing wildly as he performs. He is also seen sitting on top of, then standing next to a Chevrolet Blazer adorned with images inspired by Grand Theft Auto: Vice City; in one scene set inside what appears to be an apartment, he is seen sitting beside several women in bikinis while money rains down on him from aboveの another stage set consists entirely頭脳of a group of women in bikinis gyrating atop lowrider cars. In ラップ選手a final scene setの間では、in front 多くの時間を使ってof what appears ジェイ・Zは、to be jail cells topped with barbed wire fence, Jay-Z is then shown handcuffed and being led away by two officers; this scenes alludes to his past experience with illegal activity and police custody.

Outkast – “B.O.B. (Bombs Over Baghdad)”

Outkast’s “B.O.B. (Bombs Over Baghdad)” is widely considered one of the best hip-hop videos of 1999. The video, which was directed by Fresh Kid Ice of 2 Live Crew fame, features Outkast members Andre 3000 and Big Boi rapping in front of a giant American flag while bombs explode in the background. The video is also notable for its use of slow motion, which was used to give the impression of bombs falling in slow motion.

The Worst Hip-Hop Videos of 1999

The year is 1999. The golden age of hip-hop is in full swing. NWA, Public Enemy, and Snoop Dogg are ruling the airwaves. But not all hip-hop videos from this year are classics. In fact, some are downright terrible.

Puff Daddy – “All About the Benjamins”

The music video for Puff Daddy’s “All About the Benjamins” was heavily criticized upon its release in 1999. The video features Puff Daddy and his then-girlfriend, actress Jennifer Lopez, riding around in a sports car and flaunting their wealth. The video was accused of being insensitive to the poverty and crime that was rampant in many inner-city neighborhoods at the time.

Master P – “Make ‘Em Say Uhh!”

Master P’s “Make ‘Em Say Uhh!” video is one of the worst hip-hop videos of 1999. It features P and his Funkadelic-inspired backing band playing in front of a greenscreen, with P rapping in a faux-stutter voice and making sexually explicit gestures. The video is cheaply produced and its lack of budget is painfully obvious.

Ja Rule – “Holla Holla”

There is no denying that 1999 was a big year for hip-hop. With the release of several groundbreaking music videos, the genre was cemented as a legitimate art form. However, not every video released in 1999 was a masterpiece. In fact, some of them were downright terrible.

Ja Rule’s “Holla Holla” video is a perfect example of what not to do when making a hip-hop video. The video is cheap-looking, the lyrics are offensive, and Ja Rule comes across as nothing more than a try-hard wannabe. It’s no wonder that this video is often cited as one of the worst hip-hop videos of all time.

Will Smith – “Wild Wild West”

“Wild Wild West” is a song by American rapper Will Smith from his third solo album Big Willie Style (1997). The song features a sample of “The startled horse Jumped and ran” from the 1966 spaghetti Western film Django. The song was released as the lead single from the album on May 4, 1998. “Wild Wild West” was a commercial success, peaking at number four on the Billboard Hot 100 and number two on the UK Singles Chart. The song won the Grammy Award for Best Rap Solo Performance at the 41st Grammy Awards in 1999. The music video for “Wild Wild West” was directed by Paul Hunter and features Smith as a Victorian-era secret agent who is transported to a Wild West-themed brothel.

DMX – “Party Up (Up in Here)”

At the top of the year, DMX’s “Party Up (Up in Here)” was inescapable. The Trackmasters-produced banger was the lead single off …And Then There Was X, DMX’s third consecutive album to debut at No. 1 on the Billboard 200. You couldn’t go to a club without hearing it—or seeing its music video, which features cameos from Nas, Method Man, Redman, Ja Rule, and Mary J. Blige.

“Party Up (Up in Here)” is a great song that’s unfortunately marred by one of the cheapest-looking music videos ever made. It looks like it was shot on VHS and edited on two VCRs that were held together with duct tape. The effects are laughably bad, and there’s even a moment where DMX disappears and reappears in the same frame. It’s as if someone took a home video of a party and randomly spliced in footage from Belly for no reason.

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