 Nyorai mberi kweiyi ndima - Pashure pokuita kutanga kwake kwokutamba muCity Slickers 1991, kusarudzwa kwokutanga kwaGyllenhaal kwakanga kuri kweOctober Sky 1999, firimu rokuAmerica romuupenyu pamusoro penyanzvi yeNASA Homer Hickam. Kuita kwake semutambi wemusoro mufirimu ra2001 rekufungidzira Donnie Darko kwakamupa mubairo weYoung Hollywood uye kusarudzwa kweMweya Wakazvimirira Mubairo weMurume Akanakisa Kutungamira. Basa raGyllenhaal pamwe chete naHeath Ledger muBrokeback Mountain rakakurumbira. Kuwedzera pakugamuchira BAFTA Award for Best Actor in a Supporting Role uye MTV Movie Award for Best Performance, akasarudzwa muchikamu cheBest Supporting Actor pa 78th Academy Awards, 11th Critics Choice Awards, 10th Satellite Awards, uye 12th Screen Actors Guild Awards. Muna 2010, akabata nyeredzi mumutambo werudo wemitambo Rudo Mimwe Mishonga, zvichitungamira kune Akanakisa Mutambi mazita pa68th Golden Globe Awardsuye 15th Satellite Awards. 