Circa: 1995
Producer: Big Jaz

A year after pressing up the original, Ski-produced version of "In My Lifetime" and selling it themselves through an early version of Roc-A-Fella, Jay and Dame Dash picked up a deal with Payday Records, the hip-hop imprint run by dance music kingpin Patrick Moxey of Ultra Music. (In fact, some versions of the single actually bear the Ultra imprint). For this second, 1995 edition of the 12”, they added a remix of "In My Lifetime" from Big Jaz that was essentially an entirely new song, with a slower, more melodious, piano-driven beat and a haunting R&B chant jacked from Soul II Soul’s “Get A Life.”

Matching the probing question at the heart of the song—What’s the meaning of life?—with lyrics that justify the pursuit of money at all costs, while offering a 360-degree view of the hustling lifestyle, “In My Lifetime” 2.0 (which would later be included on the soundtrack to 1998’s Streets is Watching) set the tone for Reasonable Doubt both musically and lyrically. The original version of "In My Lifetime" had its merits, but this was the track Jay needed to finally set his career in motion after years and years of false starts.