[3] In the 2000s, Jayasurya was popular for his comic-oriented roles in Swapnakkoodu (2003), Pulival Kalyanam (2003), Chathikkatha Chanthu (2004), Kerala Cafe (2009),Chocolate (2007) and Gulumaal (2009), as well as his villainous in Classmates (2006), Arabikkatha (2007), and Kangaroo (2007) and 5 Sundarikal (2013).

He played a variety of roles in 2007–2008: the romantic lover with a comic touch in Chocolate, the serious police officer in Positive, the humorous drama scriptwriter in Shakespeare M.A.

Malayalam, the small-time thief and antagonist in LollyPop, the supporting role in Love in Singapore, and the young politician in Balachandra Menon's De Ingottu Nokkiye.

[18] In 2010 he acted in Nallavan directed by debut director Aji John, in which he played three stages of a person born and brought up on the Tamil Nadu-Kerala border.

He played the role of a paraplegic named Stephen and was well received by audiences and critics alike, all saying he has shown the best performance till date and he was one of the main contenders for best actor nominations in several film awards.

In a year-end report on Malayalam cinema, Deepika newspaper applauded Jayasurya for choosing the right roles and chose him as the Star of the Year 2011.

His role as a shady introverted pervert in Trivandrum Lodge was well received by critics and garnered more recognition for him as an established actor.

The same year his performance in Shyamaprasad's English: An Autumn in London as a Kathakali artiste-turned-waiter who is an illegal immigrant in the United Kingdom won immense critical praise.

[25] In 2014 his first release was the movie Happy Journey which was directed by Bobban Samuel, though an average grosser his performance in the role of a blind cricket player garnered praise from both critics and audiences alike.

[30][31] The same year, he acted alongside Prithviraj and Indrajith in Nadirshah's comedy movie Amar Akbar Anthony which was successful at the box office.

Jayasurya won the best actor award at the 20th Dhaka International Film festival for Sunny[37] In 2022, he starred in the investigative thriller John Luther which was directed by debutant Abhijith Joseph.