In 1998, Bobby starred opposite Neha in the Vidhu Vinod Chopra film, "Kareeb". Bobby played the character of Birju, an irresponsible young man from an upper-middle-class family in Himachal Pradesh with a love of petty thievery and deceit. Later in 1998, he appeared in Abbas Mustan's military thriller "Soldier", alongside Raakhee and Preity Zinta. Bobby played the mysterious character of Vicky, later revealed as Raju, son of Vijay Malhotra who was convicted of arms smuggling. In 1999, Bobby starred in "Dillagi", directed by and co-starring his brother Sunny Deol. The film is noted for being the first time Sunny Deol directed a film and also the first time he acted alongside Bobby. This pairing was repeated in "" (2002), "Apne" (2007) and "Yamla Pagla Deewana" (2011) among others. "Dillagi" features the two as the brothers Ranvir and Rajvir, fighting for the affection of Shalini (Urmila Matondkar).