If you have beaten the offline Showtime road rule on East Crawford Drive and didn't get the achievement you also need to beat the online time road rule.
To avoid any problems with this achievement make sure you do the offline Showtime road rule on East Crawford Drive before any other road rules on this street. If you have done any other road rules on East Crawford Drive you also need to beat the online Showtime road rule.
I'm not sure whether or not this is a glitch with the achievement or an inaccurate achievement description. Hopefully this will be fixed in a patch.