Big Boi and Dre went to high school together in East Point, Atlanta, and battled each other (lyrically) on a regular basis. They eventually teamed up, and were pursued by Organized Noize, a group of local producers who had made hits for TLC and Xscape. OutKast signed to LaFace and released "Player's Ball", which hit #1 on the Rap Chart. Their full length debut was Southernplayalisticadillakmusik (1994; see 1994 in music); the pair won Best New Rap Group at the Source Awards (1995; see 1995 in music)). ATLiens came out in 1996 (see 1996 in music) and hit #2 on the charts.
Aquemini (1998; see 1998 in music) also reached the number 2 position on the charts. Though the album had no commercially-released singles, it was widely praised as an innovative, unique and refreshing album full of gangsta rap with a progressive vision. In 1999, OutKast was sued by Rosa Parks over the album's most successful radio single, "Rosa Parks". She felt the song misappropriated her name, and also objected to some of the song's obscene language. The song's lyrics were largely unrelated to Parks, save for a line in the chorus: "Ah ha, hush that fuss / Everybody move to the back of the bus". The initial lawsuit was dismissed. Parks hired lawyer Johnny Cochran to appeal the decision in 2001, but this too was denied, on First Amendment grounds. In 2003, the Supreme Court allowed Rosa Parks to proceed with her lawsuit against OutKast.
The pair's fourth album, Stankonia (2000; see 2000 in music) was released to excellent reviews and debuted at #2. It included the single "Ms. Jackson", which is about Dre's breakup with singer Erykah Badu and became a crossover hit. Other successful singles from the album included "So Fresh, So Clean" and "B.O.B. (Bombs Over Baghdad)". All three songs' videos had heavy MTV2 airplay. OutKast also won a Grammy for Best Rap Performance by a Duo or Group for that song, and another Grammy for Stankonia as Best Rap Album.
In 2002, they released a greatest hits album, Big Boi and Dre Present... OutKast, which contained three new songs including the single, "The Whole World", which won the Grammy Award for the 2002 Best Rap Performance by a Duo or Group.
In 2003 OutKast released a double album, Speakerboxxx/The Love Below. It is essentially two solo albums packaged as a single release under the OutKast banner . Big Boi's Speakerboxxx is for the most part a joyous party record, tempered by more politically-minded tracks like 'War'. Andre 3000's The Love Below is sprawling, lush and ambitious, informed as much by Prince, Rick James and Frank Zappa as Hip-Hop; the majority of the vocals are sung rather than rapped, and much of the instrumentation is live. Both discs are highly innovative and accomplished. Speakerboxx/The Love Below has received what is perhaps the duo's most rapturous critical reception to date. The album is also OutKast's biggest commercial success yet, having debuted on the Billboard Albums Chart at number one and stayed there for several weeks. The first two singles, which were released nearly simultaneously, Big Boi's "The Way You Move" and Andre's "Hey Ya!" have both exploded at radio, Big Boi's becoming enormous on urban radio and Andre's more rock-sounding song becoming a smash crossover hit on pop and alternative rock radio. "Hey Ya!" was also one of the first songs to become a hit on the Apple iTunes Music Store, staying #1 for a months.
In a campaign commercial released October 30, 2003, the Wes Clark presidential campaign made reference to OutKast. The reference was an attempt to get the attention of a much younger generation of potential voters. In the ad, Clark is sitting in a coffee shop with a dozen middle-class young adults of various American ethnicities. The young adults do not speak, but sit and listen as Clark appears to be answering their questions. "Well, to answer your questions, no, I would not have voted for the Iraq war...I am pro-choice and I am a strong believer in Affirmative Action...And I don't care what the other candidates say, I don't think OutKast is really breaking up. Andre 3000 and Big Boi just cut solo records, that's all." The last comment prompts one of the young adults, a blonde-bearded caucasian to say approvingly "alright" and to tap fists with Clark. To avoid any doubt as to whether the commercial is hoax or not, the commercial ends with a voice-over from Clark saying "I'm Wes Clark, and I approve of this message."