In 1990 DJ Stretch Armstrong and Bobitto Garcia debuted their college radio show on Columbia University's WKCR (89.9FM) in NYC and left an indelible mark on the culture. The show, which ran until 1998, helped launch the careers of many of hip-hop’s biggest stars—including The Notorious B.I.G., Jay-Z, Nas, Big Pun, the Wu-Tang Clan, DMX, Cam’ron, Mobb Deep, Big L and Fat Joe, among others.

Listeners used to tune in to hear rare cuts, b-sides and remixes to some of their favorite songs, as well as interviews and live freestyles. Tomorrow, (early Friday morning on October 22) from 1 a.m. to 5 a.m. Stretch and Bob will return to WKCR to broadcast a special anniversary show. (Fans outside of NYC can log on to WKCR's website to hear a live stream).

We here at XXL are pretty excited by the news so to celebrate Stretch and Bobbito's 20-year anniversary we've compiled 20 of the show's more memorable freestyles. Yes, yes y'all! —Rob Markman


Big L & Jay-Z
It's not often that Jay-Z gets out-rhymed, but during this 1995 freestyle Big L was the clear MVP on the M-I-C. Now Hov was far from wack, but L was clearly the man that night. Over time, this has become the most memorable Stretch and Bob session.

Highlight: "Is Big L slow? Hell no/Bitches get fucked on the roof when I ain’t got no hotel dough." —Big L


Wu-Tang Clan
Wu-Tang Clan ain't nuthin' to fuck it and the Killa Beez proved it when they swarmed on 89.9 FM.

Highlight: "Niggas need to get shot, making watered-down hip-hop/Just to get play, mid-day at 12 'o clock." —Inspectah Deck


Nas, G-Wiz and Six Nine
Before Illmatic solidified Nasty Nas as one of hip-hop's all-time greats, the Queensbridge MC paid a visit to the Stretch Armstrong and Bobbito show to bless the mic. God's Son delivered an impromptu off-the-head freestyle and mixed in some pre-written rhymes that would later wind up on his 1994 debut. Definitely a classic hip-hop moment.

Highlight: "Deep out the skies comes the MC Nas/Not to surprise but to civilize." —Nas


Black Thought, Common, Pharoahe Monch and Absolute

Most hip-hop heads will remember this as an interlude on the Lyricist Lounge, Vol. 1 compilation that dropped in 1998, but it originated from a 1997 Stretch and Bob session. Common, Black Thought, Pharoahe Monch and the lesser-known Absolute (House of Reps) traded some ill verses back and forth raising the bar for any future MCs looking to crack the mic on WKCR.

Highlight: “The sax flow, nigga, much smoother than Coltrane/Who can cop beats that I chop like cocaine.” —Pharoahe Monch


Big Pun

Though he became the first solo Latin rapper to go platinum on his 1998 debut, Big Pun was no overnight success. The now deceased BX MC stopped through 89.9 and kicked a memorable rhyme over Smoothe Da Hustler's "Broken Language" instrumental and quickly found a spot on everyone's radar.

Highlight: "Always talkin shit, players that rather walk than pitch... Counterfeit kings of New York all on Walken's dick." —Big Pun



After his breakout appearance on Nas’ 1994 classic “Life’s a Bitch,” AZ became one of the most in demand rap rookies. In 1995 the Aziatic one blessed 89.9 with a couple of verses that would later appear on his debut album, Doe or Die.

Highlight: “My verbals rip shit, brain gives birth to thoughts in triplets/Fuck it, I’m on some flip shit, ready to let my clip spit.” —AZ


Percee P & DMX

Before getting down with the Ruff Ryders, DMX appeared alongside Percee P on WKCR. Percee was already building a reputation for kicking dope 16s, but DMX surprised listeners when he grabbed the mic and threw shots at the already established Def Squad MC K-Solo. X believed that Solo bit the concept from his 1990 single “Spellbound” from him. Oh, yeah, MF Grimm got barked on, too.

Highlight: “There’s not another getting with/The ‘Spellbound’ master ‘cause I’m hittin’ with hard rhymes.” — DMX
Big L 1998 Freestyle

Big L was the king of Stretch and Bob freestyles, hands down. During this freestyle L claimed to be tired, but still delivered a classic performance, so much so that the audio was included on his posthumous album The Big Picture in 2000.

Highlight: “I’m from broke, got enough bread/And mad hoes, ask Beavis, I get nothin’ but head.” — Big L


A-Butta & L-Swift (of Natural Elements)

In early 1996 when NYC was sacked by the one of the worst snowstorms in the city's history, local MCs A-Butta and L-Swift (two-thirds of Natural Elements) entertained the city with a witty back and forth routine.

Highlight: "I be the lyrical creature holdin' it down, choking the sound/My dick is 36 inches like the snow on the ground." —A-Butta



Common is big time now co-starring in Hollywood films with Queen Latifah and Christian Bale, but never forget that when it comes to lyrics the Chi-Town rep gets down. While he was promoting his sophomore LP Resurrection, Com paid a visit to WKCR and blessed listeners with a off the dome rhyme. GOOD music for real.

Highlight: "I'm like John Starks, nah, I'm not fuckin' up in the forth quarter/I go water." —Common


Kool G Rap & MF Grimm

During the promotional run for his 4,5,6 album, Kool G Rap and MF Grimm went up to the Stretch and Bob show to deliver one of the show's more memorable performances.

Highlight: "You want a nigga that's trickin'?/A-yo, don't look at G, I ain't no goddamn magician." —Kool G Rap


Children of the Corn

The storied NYC rhyme crew didn't make much noise outside of the city's borders as a group, but Cam'ron, Big L, Herb McGruff, and Murder Ma$e made history when they visited 89.9.

Highlight: "Stacks I'm betting 'em, bitches I'm deadin' 'em, perps I'm wettin' 'em/Niggas buying records while I'm settin' 'em." —Cam'ron


KRS-One & Lord Finesse

The story goes that Lord Finesse brought his SP-1200 up to the WKCR radio station and played some unheard beats over the air while he and Kris rocked rhymes.

Highlight: "I'm real like the Son of Sam, while others is soft like Richie Cunningham/Your styles is outdated like the running man." —Lord Finesse


Souls of Mischief & Kurious

Though the Stretch and Bob show was a NY staple, the show welcomed MCs from all regions. In 1992 Cali's Souls of Mischief sparked an on-air cypher with Harlem MC and former Columbia Records signee Kurious. No east versus west beef here.

Highlight: "Niggas can't stand this, the man is, in New York, I never chew pork." —Phesto



Das EFX’s tongue-twisting style may sound dated nowadays, but back in the early 1990’s the Hit-Squad representatives raised the bar for lyricist. When Skoob and Krazy Drayzy cracked the mic in ’93 they earned their respect with a back and forth routine.

Highlight: “Enough of that crap/Just meet me on the stage and see who can really rap.” —Krazy Drayzy


El-P, J Treds and Breezly Brewin

These indelible MCs laid the groundwork for the Def Jux era. Not only did El-P, J Treds and Breezly Brewin get down on Company Flow's "The Fire in Which You Burn," the group of subterranean MCs also blessed the Stretch and Bob show with this classic freestyle.

Highlight: "On the mic I got more presence than attendance in a class of schizophrenics." —J Treds


Smoothe Da Huslter

Brooklyn’s Smoothe Da Hustler was a force to be reckoned with when he dropped his 1995 single “Broken Language.” While his career faded rather quickly, his skills on the mic were never a question and this freestyle session proved it.

Highlight: “Peep this I kidnap Victoria for secrets to see who TLC creep with.” —Smoothe Da Hustler


Black Moon & Smif-N-Wessun

When Buckshot and company invaded 89.9 while promoting Black Moon’s debut Enta Da Stage listeners were blessed with a classic session. The oft-missing 5 Ft even made an appearance, a treat indeed.

Highlight: “You don't want it, playin' tough can earn that ass a snuff/You ain't rough, I called ya bluff and learned that you're a cream puff." —Steele


Mobb Deep

After their debut album Juvenile Hell, Mobb Deep switched their steez and stopped by the Stretch and Bob show to showcase their murderous material. Rhyming over Nas’ “The World is Yours (Remix)” instrumental, Havoc and Prodigy truly became infamous.

Highlight: “They call me Havoc, lyrical assassin with a tech/Before you step to me you rather ‘cause your own muthafuckin' death.” —Havoc
Big L & McGruff

Big L is to Stretch and Bob freestyles what Michael Jordan was to the NBA. 'Nuff said.

Highlight: “I wreck the mic, plus the whole stage/Rockin’ corn-rolled braids, I’m killin’ muthafuckas like old age." —Big L