Within the span of five short, but unforgettable years, The Notorious B.I.G. captivated rap enthusiasts with his lyrical aptitude, effortless wit and endless metaphors. Throw in pop culture references embedded in tales from the perspective of a low-level drug dealer, as well as from the vantage point of a calculated crime boss and it's clear Biggie made his mark by reaching a variety of fans.

The rapper's life may have ended at the apex of his career, but his genesis began in the hard scrabble streets of Brooklyn, N.Y., from which he would rise to become one of the borough's most celebrated sons.

Transitioning from the street life into a career in music with the help of figures like Mister Cee, DJ 50 Grand, DJ Enuff and others, Biggie would eventually join forces with Sean "Puffy" Combs in 1992, a move that would prove to be beneficial to his legacy. The first major mark he made in the industry was with the release of his debut, Ready to Die, in 1994. The Notorious B.I.G. quickly proved to be a diamond in the rough, becoming one of the biggest stars in rap and racking up a list of accomplishments, awards and other accolades while leading the charge for the east coast's resurgence.

Primed to quiet all doubters and critics with his sophomore album, Life After Death, B.I.G. would never get to fully complete the chapter, as he was gunned down in Los Angeles on March 9, 1997 in what is one of the biggest tragedies in rap history.

To celebrate Biggie's life and times, XXL has compiled 20 of the most memorable moments from his lauded career.

  • 1

    Gets Discovered by Puff Daddy

    Prior to landing a record deal, The Notorious B.I.G., then known as Biggie Smalls, was profiled in The Source magazine's "Unsigned Hype" column, which showcased up-and-coming MCs across the country. As a result, he became one of the first winners of the "Unsigned Hype" contest and his demo tape was selected by writer and A&R Matty C. This would lead to the rapper being discovered by Sean "Puffy" Combs, then A&R of Uptown Records, and the rest is history.

  • 2

    Collaborates With Super Cat for "Dolly My Baby (Remix)"

    After linking with Sean "Puffy" Combs in 1992, The Notorious B.I.G. would make his first high-profile appearance on wax in 1993, guesting on Super Cat's "Dolly My Baby (Remix)." Although Biggie's verse was brief, his appearance in the accompanying music video would put a face to the name and voice, becoming the first sighting of the rapper on a national level.

  • 3

    Releases "Party and Bullshit"

    In 1993, while signed to Uptown Records, the MC dropped his debut single, "Party and Bullshit," which was included on the soundtrack to the 1993 film Who's the Man? Produced by Easy Mo Bee, who would craft beats for much of The Notorious B.I.G.'s debut album, Ready to Die, "Party and Bullshit" was Biggie's first true buzz record and raised the rapper's profile even further.

  • 4

    Drops Debut Album Ready to Die

    Ready to Die was Biggie's claim to hip-hop fame. On Sept. 9, 1994, he released his debut album on Bad Boy Records after he and Puffy left Uptown Records the year prior. With the lone guest appearance coming courtesy of Wu-Tang Clan member Method Man on the standout track "The What," Ready to Die was a showcase of Biggie's skills as a lyricist and included everything from hit singles ("Big Poppa") to memorable album cuts ("Everyday Struggle, "Suicidal Thoughts") that now stand among the most lauded songs of the rapper's career. Ready to Die would be hailed a classic and stamp The Notorious B.I.G.'s as rap's latest superstar.

  • 5

    Goes Gold With "Juicy"

    At the outset of The Notorious B.I.G.'s career, his sole aspiration was to "go gold" and the rapper didn't have to wait long to scratch that goal off his bucket list. "Juicy," the lead single released from Ready to Die, achieved that feat before the end of 1994. Peaking at No. 27 on Billboard's Hot 100 chart, and No. 3 on the Hot Rap Singles chart, "Juicy" would be his first hit single and has since been hailed as one of the definitive rap songs of all-time.

  • 6

    Has a Son With Faith Evans

    Despite constant marital issues between Biggie and Faith Evans, and cheating on the part of the rapper, together they welcomed their son Christopher "C.J." Wallace, Jr., on Oct. 29, 1996. While this was her only child with The Notorious B.I.G., C.J., who is now 20 years old, is the sister of Biggie's other child, T'yanna. C.J. has followed in his father's footsteps and is currently pursuing a career in rap, along with other endeavors, while T'yanna launched a clothing line inspired by her dad's name. Both continue to keep the Wallace name alive.

  • 7

    Gets Married to Faith

    On Aug. 4,1994, less than a month before the release of his debut album, The Notorious B.I.G. married Faith Evans, who the rapper had first met weeks prior at Bad Boy photo shoot. The marriage would be one of the first high-profile unions between a rap artist and an R&B singer and would pave the way for the likes of Jay Z and Beyonce, and Nas and Kelis, who would also tie the knot at the peak of their careers.

  • 8

    Appears on Martin

    Known for his undeniable charisma, presence, and sense of humor, Biggie displayed all of the above during an appearance on the hit Fox TV show Martin, joining comedian Martin Lawrence for one of the more memorable moments of his career. The episode, which aired in 1995, featured The Notorious B.I.G. as an old friend of Martin Payne who was in town looking for a background singer to perform with him, ensuing in chaos and dysfunction. The spot was a testament to the rapper's potential as an actor, as his performance was as smooth as the rapper's lady-friendly singles.

  • 9

    Introduces Junior M.A.F.I.A. to the World

    Spreading love is the Brooklyn way and upon reaching success, The Notorious B.I.G. decided to pay it forward, helping Junior M.A.F.I.A., his crew of cronies from his Bed-Stuy stomping grounds, secure a record deal and release an album, 1995's Conspiracy. The group, comprised of future stars Lil' Kim and Lil' Cease, along with additional members like Trife and Larceny, Nino Brown, Chico Del Vec, Kleptomaniac, Capone and Bugsy, would score two of the biggest rap singles of 1995 in "Player's Anthem" and "Get Money." The video for the latter saw Biggie casting his mistress Charli Baltimore in the role of his wife Faith Evans, with whom he was embroiled in a marital spat with at the time. Junior M.A.F.I.A. would launch the career of Lil' Kim, who would also go on to reach multi-platinum success and become a star in her own right, carrying on the legacy of Biggie in the process.

  • 10

    Attends 1995 Source Awards

    Putting the rap world on notice with his Ready to Die album, The Notorious B.I.G. would go on a victory lap in 1995, most notably at the 1995 Source Awards, where the rapper swept many of the major categories, confirming his dominance and coronation as the king of New York. Winning the award for Best New Artist, Lyricist of the Year and the show's most prestigious honor, Album of the Year, the rapper would take the stage with his Junior M.A.F.I.A. crew and emphatically proclaim, "We did it, Brooklyn. We did it!" a nod to the borough he repped relentlessly and a signature quote that continues to resonate till this day.

  • 11

    Freestyles With 2Pac and Big Daddy Kane at Budweiser Super Fest

    Biggie and 2Pac would become the faces of the East Coast vs. West Coast beef that dominated the mid 1990s, but prior to becoming at odds with one another, they considered each other kindred spirits, building a quick friendship and collaborating on records together. However, their most iconic moment together is their appearance alongside Big Daddy Kane, Skoob and a young Shyheim for a freestyle at the 1993 Budweiser Super Fest. Spouting off a rhyme that is considered one of the premier couplets ever to be spat live on stage, The Notorious B.I.G. may have been the lesser known artist, but proved his worth and ability to hang with the best and was a landmark moment in the rapper's young career.

  • 12

    Appears on Craig Mack's "Flava in Ya Ear (Remix)"

    "Niggas is ass, I get more butt than ashtrays," The Notorious B.I.G. raps on "Flava in Ya Ear (Remix)" a single from label mate Craig Mack's Project: Funk Da World album, which would help revolutionize the art of the rap remix. Pitted against heavyweights like LL Cool J and Busta Rhymes, The Notorious B.I.G. asserted himself, accounting for arguably the best verse on the entire song and one of his greatest guest appearances.

  • 13

    Links Up With Jay Z for "Brooklyn's Finest"

    During The Notorious B.I.G.'s ascent to stardom, a then-unknown Jay Z was fighting to rise through the rap ranks himself, putting his money where his mouth was, forming Roc-A-Fella Records and releasing his debut album, Reasonable Doubt, in June 1996. Biggie, who took a liking to Hov's style and lyrical flair, gave his Bed-Stuy brethren a huge cosign by appearing on "Brooklyn's Finest," one of the LP's premier selections. Although The Notorious B.I.G. and Jay Z would only collaborate three times before Biggie's untimely death, Jigga would keep his comrades name alive and pick up the torch as the new king of rap in the wake of his passing.

  • 14

    Puts Out "One More Chance (Stay With Me Remix)" Music Video

    After scoring hit singles with "Juicy" and "Big Poppa," The Notorious B.I.G. hit a homerun with the release of "One More Chance (Stay With Me Remix)," which would become the rapper's highest-charting single at that point in time. Featuring appearances from Faith Evans and background vocals from Mary J. Blige, "One More Chance (Stay With Me Remix)" would peak at No. 2 on the Billboard Hot 100 chart and be accompanied by a star-studded music video, which included cameos from the biggest stars in rap, R&B and beyond.

  • 15

    Records With Micheal Jackson

    Only a handful of rappers have had the pleasure of appearing on a Michael Jackson song, one of them being The Notorious B.I.G. After achieving mainstream success, Biggie was tapped to appear on Michael Jackson's 1995 album, HIStory, on the song "This Time Around," providing one of the more underrated guest verses during his prime. "This Time Around" would not be a single, but The Notorious one's connection to the King of Pop would inspire artists like Jay Z to also affiliate themselves with Michael Jackson, another testament to the Brooklyn heavy's influence.

  • 16

    Joins Total for "Can't You See"

    In 1995, Bad Boy Records began to unleash its stable of R&B talent, which included the group Total, whom The Notorious B.I.G. gave an assist to by tacking on a verse to the trio's debut single "Can't You See." Peaking at No. 13 on the Billboard Hot 100, "Can't You See" would be the first of a string of appearances on R&B records for Biggie, and is possibly the greatest of them all.

  • 17

    Releases "Who Shot Ya"

    Following the shooting of Tupac Shakur at Quad Recording Studios in New York, in 1994, The Notorious B.I.G. released a track titled "Who Shot Ya?" a song that would have lasting ramifications and help alter the course of rap. Shakur felt The Notorious B.I.G. and the Bad Boy Records family, who were also present at the studio at the time of the shooting, had been aware of the robbery that occurred and had failed to warn him. He deemed Biggie's "Who Shot Ya?" as a taunt, setting in motion the East Coast vs. West Coast rap beef. The Notorious B.I.G. and Sean "Puffy" Combs would contend that the song was recorded prior to the shooting and was in no way related to or inspired by the studio shooting. The track, which is also among Biggie's premier offerings, has since been shrouded in controversy.

  • 18

    Gets Into Car Accident

    The Notorious B.I.G. was involved in a serious car accident in New Jersey in 1996. The incident left the hefty rapper with a shattered leg and Lil' Cease, who was the driver of the car, with a shattered jaw. Biggie, in humorous fashion, would famously reference the accident in freestyles, as well as on his Life After Death album, on the song "Long Kiss Goodnight," rapping, "Ya still tickle me, I used to be as strong as Ripple be/Til Lil' Cease." Due to the accident, The Notorious B.I.G. would be required to walk with a cane until the time of his death.

  • 19

    Shares "Hypnotize" Music Video

    Filmed in February 1997, a month prior to The Notorious B.I.G.'s death, "Hypnotize" would be the last music video the rapper appeared in. Directed by Paul Hunter and shot in Los Angeles, the visual would accompany the release of the song, which arrived on March 1, 1997, and would be The Notorious B.I.G.'s first single to top the Billboard Hot 100 chart.

  • 20

    Lets Loose His Sophomore Album Life After Death

    Two weeks after The Notorious B.I.G.'s death on March 9, 1997, the rapper's sophomore album, Life After Death, was released posthumously on March 25. The project would peak at No. 1 on the Billboard 200 a week after its release. A double-disc album, Life After Death would feature an evolution in the sound and lyrical content of The Notorious B.I.G., with Bad Boy's in-house production squad, The Hitmen, supplying him with plush, cinematic soundbeds to craft a number of classic records over. Certified Diamond with over 5,000,000 units sold, Life After Death is regarded as one of the greatest bodies of work in the history of hip-hop and cemented The Notorious B.I.G.'s status as one of the greatest rappers in the history of the genre.

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