$hort Dog and Dangerous Music were enjoying tremendous success, and $hort had no major interest in signing with a major label. He may have been more of a regional star, but $hort was in his comfort zone. But the prospect of "going national" intrigued him. He'd released 1987's Born To Mack on his own Dangerous Music label, but it was after several years of building a local following via his indie releases. Born To Mack sold 50,000 copies throughout the Bay Area without radio play or traditional promotion.

"When I signed to Jive Records, I was probably eight years into being a rapper," $hort told VladTV in 2022. "From 14-15, when I really got rolling, and when I signed to Jive, I might've been 21-22, somewhere in there. 1988, in 1987, when I made my fourth album, the first three had been underground albums on a label called 75 Girls Records. It was owned by a dude named Dean Hodges from the Acorn Projects in West Oakland. Dean was a well-known street hustler who did good and he was upper echelon in the hustling world."

$hort's connections to Dean, who was eager to launch a music label, led to the young rhymer landing with some of his hometown's best musicians and engineers.

"I was ready," $hort explained. "Dean showed me [how to] get my feet wet."

Originally released on cassette and vinyl, Life Is... serves as a love letter to $hort's hometown of Oakland. The album is split between two sides: The "Todd Shaw" side and the "Too $hort" side. The rapper's intention was to make this project an intro of sorts to those who hadn't been up on just exactly who this Too $hort guy was. He recognized the importance of Life Is...Too $hort long before the album reached it's double-platinum-selling peak. Everyone was aware from its very inception that this album would be major for Too $hort.

$hort himself handles most of the album’s production, with an assist from Dangerous Music's core of producers/musicians Al Eaton, Ted Bohannon, and Randy Austin. The Todd Shaw half of the album features the rapper's commentary on coming up; making a name for himself as both an artist and an entrepreneur. The Too $hort half of the project leans into his horny pimped-out persona, displaying his knack for raunchy raps and freaky tales.

“Rhymes” is the most Run-D.M.C.-esque track on Life Is..., and highlights the influence the Kings from Queens have had on artists far beyond their NYC homebase. “Don’t Fight the Feelin’" flips the One Way track of the same name, with $hort going all in with his nasty rhymes: Barbie of the local female duo Danger Zone and Rappin-4-Tay show up to assist on the kind of track that would have $hort trending today for all the wrong reasons.

"I Ain't Trippin'" is a semi-autobiographical look at $hort's journey up to that point, and the pitfalls and hard lessons he's learned from former friends. The music video features $hort highlighting life in Oaktown; his success put him in rarified are in his home city, but it also would serve as a guiding light. It also features comedian and fellow Oakland product Mark Curry, humorously dissing Too $hort as a hater jealous of the rap star's rise and spreading rumors. "Cuss Words" became one of his most notorious tracks: $hort Dog became famous for saying some of the most salaciously X-rated lyrics on wax, and he revels in his infamy on one of the album's standout moments.

"City Of Dope" is a commentary on the crack epidemic in Oakland, as seen through Too $hort's eyes.

The album's title track would become an unofficial theme song for Too $hort, and it's music video would be the first from the rap superstar to enjoy major airplay on high-profile networks like MTV and BET. "Life Is...Too $hort" eventually became a touchstone for many, everyone from UGK to $hort himself has referenced the track, which famously flips the riff from "Schoolboy Crush" The Average White Band.

The success of Life Is... put Too $hort on another plateau. The album remains his best-selling to date, and it set the table for a generation of Bay Area artists to land major deals. By the dawn of the 1990s, Bay Area Hip-Hop was thriving on the national stage. And a lot of that had to do with the success of Life Is...Too $hort.

"I've always been a trailblazer for Bay Area music," $hort said in 2022. "And I feel like I wasn't thinking like that at the time; but by me signing to Jive Records and being probably the first rapper from the Bay to go to a major label, it just opened the floodgates for others to go 'Man, I think Imma jump in.' Which, as everybody jumped in, a few of them did go to Jive Records: Spice-1, E-40, a lotta people like Ant Banks came along with me, Pooh Man did an album through Jive."