His first major film debut was Close to You, produced by ABS-CBN subsidiary Star Cinema and co-starring John Lloyd Cruz and Bea Alonzo.

His first major solo concert, "Sam Milby: Rockoustic Heartthrob", occurred at the Aliw Theater on October 25, 2008.

[citation needed] In 2012, Milby spent three months in the United States, taking part in auditions in New York.

He also performed in concerts and tours, playing Lazarus for one night in the Broadway musical Godspell, and guest-starring in Anna Maria's Benefit Concert in New York with Anna Maria's Godspell costars Corbin Bleu, Wallace Smith, Nick Blaemire, Eric Krop, and George Salazar.

[4] Milby took part in the Cannes Film Festival in 2013, where the Adolfo Alix Jr. movie Death March, in which he had acted, was screened in Un Certain Regard section.