Started working when I was nine for my grandfather doing manual labor. My first job for a company was at my uncle's laundromat when I was twelve doing mopping and cleaning, then I served as a law clerk the week after I turned 16, and worked there until I quit and couldn't find a job for three months in 2008.
So three months is the longest.
During that time, though, I did manual labor again just to get out and keep myself busy, even if it was for meager change, while at night I job hunted and took off necessary days for interviews. Been employed since.