Highs & Lows From Cassidy's Career

From hit songs with R. Kelly to a murder case and near-fatal car accident, we plot the highs and lows of Cassidy's music and battle rap career.

Depending on who you ask, Cassidy is either returning to his roots or succumbing to a late-career lowpoint by agreeing to battle Dizaster at FilmOn's "Ether" event this weekend. When Joe Budden faced off against Hollow Da Don in July he became the year's first big-name industry head to enter the ring and officially he was also the first celebrity loser. And by most accounts, unofficially too ... Dropping the mic and stomping off mid-battle doesn't go over well with the battle rap community.

Cassidy has been hyping himself up his whole career, a witty braggadocio essential to his public image and much of his recorded material. Still, unless you let Cass tell it, he never made as lasting an impact as some of his Philadelphia cohorts, a couple mainstream radio hits notwithstanding.

With Cassidy finally taking a battle against Dizaster — after months of claiming he was above and beyond battle rap and its measly payouts — BattleRap.com decided to plot out his career's highs and lows ourselves. There was the R. Kelly collab, his infamous battle against Freeway, that near-deadly car accident, and plenty more. For Dizaster's career high and lows, click here.

One thing's for sure: Cassidy hasn't been truly on top for a long time and his second-wind output is full of rushed remixes to just released hits. The foray into battling might be just a quick payday, but with the music industry flailing like never before, maybe there's more to Cassidy linking up with FilmOn. Whether or not he'll live up to the high expectations he's built for himself, Cassidy has already had more than a decade of highs and lows.

Here's at least some of them:

Battle Rap History

When Cassidy's name gets brought up within the context of battle rap it's usually because of his faceoff against fellow Philly rapper Freeway. The match-up hasn't aged particularly well — shoddy video footage from 2001 rarely does — but it does offer a glimpse into how far battle rap has come. It's also important to remember that Cassidy was 19 years old at the time and his name is still ringing out. Still, if he comes at Dizaster with the same style he built his legacy on, he might be playing the same part Freeway did by the third round.

"In A Hotel, Not The Motel, Or The Holiday Inn"

If you have only a passing familiarity with Cassidy, it's probably off the strength of his 2003 hit single "Hotel." Producer Swizz Beatz signed Cassidy to his new Ruff Ryders affiliated sublabel Full Surface in the early aughts as its first artist. At the time, Swizz Beatz was well on his way and the R. Kelly feature yielded Cass one of his biggest singles ever even with it being his first.

The track was pulled from the Philly emcee's debut album Split Personality, a project that featured another seven added Swizzy beats and features from Snoop Dogg, Jada Kiss, Jazze Pha, and Trina. The album went Gold in its first week and propelled Cassidy's more than decade-long career.

Murder Case, Arrest & Car Accident

In 2005, Cassidy and two other men apparently got in an argument and shot three unarmed men, killing one. The shooting took place in Northwest Philly and landed Cassidy in jail a couple months later while he awaited trial for murder, attempted murder, reckless endangerment, and other related charges. If he'd been convicted, he would have faced life in prison and potentially the death penalty. A witness eventually withdrew their statement and Cass' charges were lowered considerably, eventually leading to a conviction for involuntary manslaughter, aggravated assault, and a gun charge. He ended up serving a total of eight months before being released in the winter of 2006.

Several months later, in October, Cassidy got in a serious car accident and was left in a coma for a week. He still has scars from the accident and initially suffered from short-term amnesia upon waking up from the coma.

In the interview below he talks about both incidents.

More Mainstream Success ... And Then Decline

Nothing after Split Personality was as big a success, but Cassidy's second album (and single of the same name) in 2005 solidified him as a capable, street-minded emcee. Its title track "I'm A Hustla" fueled a slew of big-time remixes, as did his 2007 single "My Drink N My 2 Step" which hit #11 on the Hot RnB/Hip-Hop chart.

After his arrest and release a few years later, Cassidy's third album saw Swizz Beatz sticking with him to the end of his mainstream appeal.

By 2009, Cassidy signed with Carmelo Anthony's Krossover Entertainment record label, which didn't do much for his career at all.

"Condom Style"

There's not much to say about this. It'd be one thing if Cass was doing more serious and legitimate public health outreach (though that would still be the source of plenty of jokes), but this is more of an embarrassing jingle. It's also a not-so-clever "Gangnam Style" remix, which makes it that much worse.

Cassidy's been saying the battle rap money hasn't been enticing enough for him to return over the last couple years. Which makes us wonder, how much did he get paid for this one?

Meek Mill Beef: "RAID" And Resolution

A beef with fellow Philly rapper Meek Mill turned into an extended back-and-forth last year, and while there wasn't an official battle in the end, the diss tracks that resulted proved that Cassidy is still on his game when it comes to the lyrical attack. Earlier this year Cass admitted to moving on and addressed the way the media handled the rift, but his "RAID" diss aimed at Meek may be the most lasting piece of the spat and some final proof that the veteran Philly rapper hasn't lost a step.

Leading up to his battle against Dizaster, "RAID" is likely where all the fans pulling for Cassidy will point in making their case that he's a serious contender.

Return To Battle Rap

Whether or not Cassidy wins against Dizaster at "Ether," he's set himself up for a big paycheck either way, and his return to the ring has his name ringing out more than it has in the past few years otherwise. To a certain degree, Joe Budden proved in July that a foray into battling can be a career win regardless of the performance, and with a reported $250k payday for Cass either way, it's hard to consider his return as anything but smart business at this point. Whether or not he wins, the once street-bound rapper from Philly has positioned himself for a late-career renaissance. His performance at "Ether" will be closely watched by fans and detractors alike, and no doubt his next steps depend on how he fares against Diz this weekend.

What do you think? Did we miss anything from Cassidy's career that deserves to be on this list? Let us know in the comments. 

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