Possible Clues:

• *Justin Timberlake hit of 2002 (... letters 5-7)
• 2002 hit for Justin Timberlake
• 'Oh, boohoo!'
• Torch song made famous by Julie London
• 1950s torch song made popular by Julie London
• *1955 hit for Julie London
• 1955 Julie London hit
• Single for Julie London in 1955 and Justin Timberlake in 2002
• 1955 hit song ("okay, but it won't be easy")