Hozirda 'The Daily Show w/ Trevor Noah' dasturida muxbir sifatida faoliyat yuritayotgan Roy, Hollywood Reporter tomonidan "Ajralib turuvchi" deb ta'riflangan, Entertainment Weekly esa uning fikrni qiziqtiruvchi komediyasini "jozibali g'azab" deb atagan. 2016 yilda 'Variety' jurnali uni kuzatish kerak bo'lgan 10 komikdan biri deb e'lon qildi. 'The Daily Show' dan oldin Roy TBS'ning sitcomi 'Sullivan and Son' da uch yil ishlagan. Hozirda u 'Conan', ESPN'ning 'SportsNation' va Comedy Central'ning @Midnight dasturlarida muntazam ishtirok etmoqda. Alabama shtatining Birmingem shahrida tug'ilgan Roy, 1998 yilda 19 yoshida Florida A&M universitetida o'qiyotganda komediya faoliyatini boshlagan. U 2006 yilda 'The Late Show with David Letterman' dasturida televizion debyutini amalga oshirdi va 2010 yilda 'Last Comic Standing' musobaqasida uchinchi o'rinni egalladi. Shuningdek, u HBO'ning 'Def Comedy Jam', Comedy Central'ning 'Premium Blend' va 'The Late, Late Show with Craig Ferguson' dasturlarida ham qatnashgan. Bundan tashqari, u 2006 yilda Montreal Just for Laughs komediya festivalida "Yangi yuzlar ko'rgazmasi"da ishtirok etgan. 2006 yilda Wood Comedy Central'da Bob va Tom Radio Show: The Comedy Tour dasturida qatnashdi. Shuningdek, Roy 2001-2012 yillarda radio sohasida ham faoliyat yuritgan va uning ertalabki shousi Alabama Broadcasting Association tomonidan 'Eng yaxshi katta bozor ertalabki shousi' nominatsiyasida mukofotlarga sazovor bo'lgan. Wood uchta milliy tarqatilgan prank qo'ng'iroq CD'sini yozib olgan: 'My Momma Made Me Wear This' (2003), 'Confessions of a High School Bench Warmer' (2005) va 'I'll Slap You to Sleep!' (2009). Yaqinda esa u o'zining birinchi komediya CD'si 'Things I think, I think' (2013) ni chiqardi.
