It’s ironic that Philadelphia emcee Meek Mill is releasing his debut album, Dreams & Nightmares, the same week as Halloween. Not just because of the name of the album, but because of something much more woeful.

Despite being known for producing some of the most respected lyricists in Hip-Hop, over the last 20 years, Philly has only seen two of its hometown emcees successfully cross into the mainstream. Not since the haydays of Eve has a rapper from the city of brotherly love been a household name. Before that, it was The Fresh Prince—Will Smith.

Legal issues, souring industry relationships and, in some cases, flat out bad luck have plagued almost every Philadelphia emcee who has been poised for major crossover success. When it comes to the number of Philly rappers who have watched their opportunities come and go, ‘misfortune’ might an understatement. It’s almost curse-like.

Mill is looking to break this foul pattern.

Before the Billboard Hot 100 singles, collaborations with legendary pop divas and signing a major recording contract with one of the most popular artists in hip-hop, Mill grew his buzz by releasing one impressive project after another, becoming the “next big thing” in the streets of Philadelphia.

His Flamers mixtape series spawned local hits like “In My Bag,” “Hottest in Tha City” and “Make ‘Em Say,” attracting suitors from major record labels in the process. His energetic voice, paired with the natural grit of the Philly hip-hop scene, made his music appealing to many, including T.I.—who originally looked to sign Mill in 2008—years before Rick Ross. Both T.I. and Mill, however, would serve jail time on separate weapons charges over the next two years, slowing down the Philadelphia emcee’s momentum he garnered after the Tip’s co-sign. This opened the door for Ross, who, after appearing on the remix to “Rosé Red,” continued talks with Mill and signed him along with Wale to his imprint in February of 2011.

Nowadays, thanks to records like “Tupac Back,” “Ima Boss,” “Burn” and “Young & Gettin’ it,” the 25-year-old is widely viewed as one of the most popular hip-hop acts in the industry. And despite a brief controversy with a Philadelphia pastor over the lyrical content in Mill’s Drake-assisted lead single, “Amen,” the song is still on the Billboard Hot 100 after 18 weeks.

With his current popularity and success, Mill has an opportunity to tap into a mainstream audience that most Philadelphia rappers haven’t been able to reach.

Cassidy was once revered as one of the best freestylers and overall lyricists in hip-hop, but struggled to produce solid albums and had to serve time in prison during the prime of his career. E. Ness received major exposure on MTV’s Making Da Band 2, but Diddy’s reality group only lasted one album, leaving Ness to try his luck again on the mixtape scene and battle rap circuit. Black Thought of The Roots has recorded Grammy-award winning music with his bandmates, but is often overshadowed by the drummer in his own group and never really looked at as a star himself.

And though they played an integral part in the glory years of Roc-A-Fella, none of the members of State Property were able to achieve any substantial mainstream success. Some argue that Beanie Sigel was just as talented lyrically as Jay-Z and outrapped him on several occasions, including tracks like “Guess Who’s Back” and “Still Got Love for You.” Despite his lyrical prowess, though, legal trouble and stints in prison have continuously hampered his career. Freeway and Young Chris were also viewed as emcees of great caliber, but like the rest of SP, their best opportunities faded after the Roc-A-Fella split.

Mill’s debut album and subsequent projects are important if he wants to break this unfortunate trend, and he’s certainly put himself in good position to do so.

He’s signed to one of the most popular rap stables in hip-hop, has a management deal with Jay-Z’s Roc Nation as well as endorsements with Skullcandy headphones and PUMA. It would also appear that Mill has the support of Will Smith, as the rapper-turned-actor was present at the NYC Dreams & Nightmares listening session. There’s no co-sign bigger for a Philadelphia artist.

Meek Mill’s career has already seen its share of ups and downs, but with the support system he has around him and his ability to make catchy, high-energy music, he could very well be the one who ends Philly’s ill-fated drought.