Label They Almost Signed To: Def Jam
Label They Ended Up Signing To: Interscope
Circa: 2005

Back in the middle of the ’00s, when Jay-Z was president of Def Jam, a young, sneaker-obsessed rapper from Washington D.C. caught his eye (or ear). His name was Wale, and every rap hopeful’s dream looked ready to come true for him—until Jay relinquished his post to return to rap with Kingdom Come. "I met Jay-Z three years ago when he was at Def Jam," said Wale, on The Mo' Nique Show. "I almost had a situation there but he left." Wale would sign to Interscope, and eventually MMG, but he's still managed by Roc Nation—a remnant of what might have been.