Article continues below advertisementCharlie Sheen and Jon Cryer Worked Together on 'Two and a Half Men'Source: MEGACharlie Sheen and Jon Cryer costarred on 'Two and a Half Men' for eight seasons.Charlie Sheen and Jon Cryer's friendship has gone through a turbulent phase over the past years.In 2003, Sheen and Cryer worked together on the hit sitcom Two and a Half Men, portraying brothers Charlie Harper and Alan Harper, respectively.According to The Famous Teddy Z star, the early years with Sheen on the show were "great.