Shailendra Singh was born in a Punjabi Family. He studies at Hill Grange High School and graduated from St. Xavier’s College, Mumbai. After graduation, he joined the Film and Television Institute of India to take training in acting.
He made his Bollywood debut as a singer through the movie Bobby. He was still in 2nd year at the FTII when he sang in the movie Bobby. Singh did not have a much successful career. He sang in several Hindi and few Marathi songs in the 70s and 80s. He sang in many movies like Bobby, Do Jasoos, AapkiKhatir, Aar Par, Ab Kya Hoga, KhattaMetha, Amar Akhbar Anthony, AmiriGaribi, Amma, BegunahQuaidi, Sagar, BholeShanker and many more. It was said that his voice most suited to Rishi Kapoor.
Shailendra Singh had many hits in his basket. The first break was given to him by none other than Raj Kapoor in the movie Bobby. The song “Main ShayarTohNai” became a great hit. His next song “HumneTumkoDekha” from the movie Khel- Khel Mei made the whole nation dance. The fame he got was not for long period of time. He acted in some movies like Agreement opposite Rekha and Do Jasoos but those movies did not work for him. He also acted in few Marathi and Bengali movies. His career started fading after the decade of the 90’s and he did not make any comeback.