Possible Clues:

• Dragster, e.g
• 1988 Tracy Chapman hit with the lyric 'We go cruising, entertain ourselves'
• 1988 top 10 hit for Tracy Chapman
• Speedster
• Tracy Chapman hit with the line 'I had a feeling I could be someone'
• Tracy Chapman hit with the line "Won't have to drive too far"
• Drag race vehicle
• Maserati, e.g.