In 1998, Upendra directed and starred in "A", which was his fifth film as a director but his first lead role as a hero. The film had a 175-day run and became a trend-setting blockbuster in Karnataka, with its Telugu dubbed version running for 100 days in Andhra Pradesh. Around this time, he received an offer from Amitabh Bachchan Corporation to make a film for them, which did not materialize. Due to Upendra's newly found popularity in Telugu, Telugu director E. V. V. Satyanarayana cast him in the 1998 Telugu film "Kanyadanam" alongside Srikanth and Rachana, which also became a commercial success. In 1999 Upendra again directed and starred in his self-titled film "Upendra" which starred Bollywood actress Raveena Tandon. The film went on to become a bigger hit than "A", both in Karnataka as well as in Andhra Pradesh. The film had a 200 days run in Karnataka and 100 days run in Andhra Pradesh. In 2000, Upendra starred opposite Bollywood actress Sonali Bendre in the psychological thriller "Preethse" which was a remake of Bollywood film "Darr". "Preethse" became Upendra's third consecutive blockbuster that ran for 175 days. With three back-to-back highly received films, Upendra became well known in the Kannada and Telugu film industries. In 2001 Upendra wrote and starred in a Telugu film titled "Raa," which became a box office hit in Andhra Pradesh. "Raa" was a typical Upendra style film in which he plays a womanizing playboy. Upendra starred opposite his future wife Priyanka Trivedi for the first time in this film.