In 1998, Lazlow lived in Liberty City and hosted "Chatterbox", a talk show on Liberty City Free Radio where he took calls from random listeners and interviewed eccentric guests. It is hinted by some of the comments he makes on Chatterbox FM in Grand Theft Auto III that in between his job in GTA: San Andreas and his appearance in Grand Theft Auto: Liberty City Stories circa 1998, he was working in Malaysia digging sewage ditches just outside of Kuala Lumpur. Lazlow lost his WCTR job due to alcoholism and possibly drug abuse sometime after the events of Grand Theft Auto: San Andreas. Judging by his comments later on the radio, it is implied that in between 19 he developed problems with drugs and alcohol, and that he did something to his mother that is illegal in most states. He seemed to be somewhat out of touch and confused about the new media trends at this point, as in his interview with OG Loc he thought that contemporary rappers still did windmills and other '80s breakdance moves, and when his misunderstandings make OG Loc so angry that he points a gun at him, Lazlow, clearly panicked, tries to fix things claiming he is "just coming down from the 80s". Lazlow re-emerged in 1992 on the national scene as the new host of the Los Santos-based syndicated West Coast Talk Radio show Entertaining America, replacing the original host Billy Dexter after his untimely accidental death at the hands of a roid-raging Jack Howitzer.
At one point, he became so desperate, Lazlow called the radio show I Say/You Say begging for work.