By Brittany Hutson

Nowadays, when music artists get the itch to step away from the industry and dive into the world of entrepreneurship, it’s pretty much no surprise that their first venture is a clothing line. But according to Kristin Bentz, retail analyst and president of Talented Blonde, LLC, “the era of the celeb-designer is close to being over, if not already. When the recession hit, so many rappers/actors/personalities rushed to get licensing deals. So now we are overrun at retail with the remnants of rappers past.”

We collaborated with Bentz to critique some of hip-hop’s hottest lines that are still memorable today, not only for their sales, but also for their massive appeal to consumers and demonstrated business savvy on the part of the artist; as well as some of hip-hop’s less memorable brands due to high pricing points, an absence of solid promotion and mismanagement.

Here are Bentz’s picks for fashion lines that have been leaders in the artist-designer arena:

Phat Farm

Russell Simmons was undoubtedly the pioneer of the celeb-designer phenomenon with the launch of Phat Farm in 1992, which combined the urban aesthetics of the streets and the preppy culture of the Ivy League for men. Successful lines such as Phat Farm are “established by tier one rapper/artists that truly have the star power and financial backing to hire superior management teams and designers, as well as [finance] multi-million dollar ad campaigns,” says Bentz. Another example the demonstrates Simmons’ business savvy and why the brand has lasted for nearly two decades was his decision to sell Phat Farm to the Kellwood Company in 2004 for $140 million. “Brands are sold to large publicly-held companies that know how to merchandise, manage and promote a brand much better than the celebs who own the company are able to.”

By Barbara Thau

“From the block to the boardroom.” That’s where Sean John, the sportswear line from Sean “Diddy” Combs, is headed, says the hip-hop-mogul-turned-fashion- designer. And Combs is betting big on Macy’s to take it there.  Come spring 2011, Macy’s will be the only U.S. department store to sell the 11-year old sportswear brand, which has morphed from an urban, young men’s line synonymous with sweat suits, into a modern collection that cultivates sophistication.

The exclusive deal marks Sean John’s bid to revive its appeal with shoppers who have evolved, just like Combs himself, Sean John and Macy’s executives said. The partnership is also designed to woo younger consumers to the brand and reignite sales of the line.

In turn, Sean John, which Macy’s has carried since 1999, will be discontinued at department stores such as Dillard’s, Bon-Ton and Belk, as well as specialty stores like Jimmy Jazz. Sean John, the line’s eponymous fashion company Combs founded, is counting on the heft and scale of Macy’s to take the sportswear part of the brand to new heights.

“Macy’s has a huge reach,” said Dawn Robertson, president. “We believe there’s a substantial growth opportunity with Macy’s.” She added: “We would not have given up distribution in department and specialty stores…if we didn’t think we could get a lot of top line growth, because it’s about top-line growth in the end.”

The brand has generated $1 billion in sales at the chain since its 1999 debut, Combs said during a May press event to launch the line at the Standard Hotel in Manhattan’s ultra-hip Meatpacking District neighborhood. Exclusive Sean John woven sport shirts, knits, sweaters, t-shirts, denim, vests, pants, shorts, outerwear, jackets and sport coats will be sold on macys.com and in 400 Macy’s stores next spring, with plans to roll out the line to most of Macy’s 850 doors over time.

“This is one of the biggest business moves of my life,” Combs said. And the Macy’s deal is designed to fortify his fashion-insider status. It’s one facet of Combs’ methodical efforts to burnish an image as a multi-industry renaissance man.

That drive has culminated this year with launch of a new album in June that has him “doing things with my voice that I’ve never done before,” as well as a starring role in the film, “Get Him to the Greek,” said Combs, who apologized for his hoarseness during the press conference.

That’s a far cry image-wise from the “Puff Daddy” of the late 1990s, who was embroiled in a high-profile shooting incident at a New York City club—but was later cleared of all charges. It also brings the 40-year old Combs, who recalled working at Macy’s when he was 16, selling shirts and ties, full circle. “The evolution of the Sean John brand mirrors the evolution of Diddy,” said Kevin Morrissey, executive vice president and general merchandise manager of men’s for Macy’s. “This initially was a line that was targeted at the younger urban customer who has grown with the brand and who now is looking for more modern, professional fashion,” he said.

The line’s appeal spans “all demographic groups,” said Jeff Gennette, Macy’s chief merchandising officer. “Everybody wants to look like Sean.” But in recent years, the Sean John brand had lost some of its luster. After a period of “phenomenal growth,” the collection had hit a wall, and wasn’t growing, Robertson said. The company set out to “reinvent” the brand in 2008, going beyond its urban roots toward a more contemporary collection “that you can wear in most occasions in your life,” she said.