After his break-up with Williams, in late 2007 and early 2008, the tabloid press and other public media linked Ledger romantically with supermodels Helena Christensen and Gemma Ward. On 30 January 2011, Ward stated that the pair began dating in November 2007 and their families spent Christmas together in their home town of Perth.
Ledger had aspirations to become a film director and had made some music videos with his production company The Masses, which director Todd Haynes praised highly in his tribute to Ledger upon accepting the ISP Robert Altman Award, which Ledger posthumously shared, on 23 February 2008. In 2006, Ledger directed music videos for the title track on Australian hip hop artist N'fa's CD debut solo album Cause An Effect and for the single "Seduction Is Evil (She's Hot)". Later that year, Ledger inaugurated a new record label, The Masses Music, with singer Ben Harper and also directed a music video for Harper's song "Morning Yearning".
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^ Nick Squires (1 April 2008). "Heath Ledger 'fathered a secret love child' ". The Daily Telegraph. UK. Retrieved 6 August 2008. If the claims are proved to be true, Ledger's multi-million pound estate would have to be divided between the child he fathered in his teens and his two-year-old daughter, Matilda Rose, whose mother is Hollywood actress Michelle Williams. ... The actor's parents, Kim and Sally Ledger, have declined to comment on the reports [based on comments by other family members, including his uncle Haydn Ledger].