Gurera was born on 30 August 1965 in Moga, Punjab (India). He started his per-university (11th) from DAV College, Abohar, but graduated with a degree in Science from Multani Mal Modi College at Patiala in 1986. After shifting Gurgaon, Haryana got the degree in Applied Arts from College of Art at New Delhi in 1990.
During 1973 Gurera's first cartoon was published in Veer Pratap (then leading newspaper in Hindi from Punjab) as he was awarded in an on the spot competition. During his school days he continued his skill of cartooning and sketching as hobby only. During 1984 he professionally started contributing to Punjab Kesari as freelancer while pursuing Science graduation at Patiala.
During his graduation he secured four University Colors and Gold Medals in Cartooning and Sketching where as in 1982 while being a student of 11th he was honored by the Speaker of the Lok Sabha, Balram Jakhar. In 1989 he was honored by the PM, Rajiv Gandhi; In 1990, by The President, Giani Zail Singh and in 1992 with the Best Cartoonist Award by the PM P. V. Narasimha Rao during 1st Babu Jagjeevan Ram Memorial All India Art Exhibition. In 1996 awarded for the Excellence in Cartooning at 20th Matri Shree Media Awards, by the Delhi CM Sahib Singh Verma. In 1997 he got honor to represent India at the 3rd Asian Cartoon and Art Exhibition conducted by The Japan Foundation at Tokyo, where as in 2002 he was awarded by The Saitama's Humor Photo Contest, Japan. In 2011 he was honored at Mahamana Madan Mohan Malaviya Memorial 7th Annual Award for Journalism (Cartoonist).
In 1999, Shekhar drew a series of Kargil Kartoons, on-the-spot cartoons of Indian soldiers passing through the New Delhi railway station on their way to Kargil. The cartoons on the Kargil War were later exhibited at The Lalit Kala Academy, New Delhi on 25–31 July 1999, followed by the chain exhibition of cartoons at Jaipur, Chandigarh, Patna and Indore.
From 2001 onward, carrying a unique weekly feature, Future Lens, which is very popular abroad as well. This column features a popular celebrity from sports, films, politics or other fields and depicts them as they'd look with 30 years added to their present age. These pictures are created by painting digitally, which makes them look like actual photographs.
A chain of cartoons for the Calendar 2005 and 2016 of National Productivity Council while defining the different ways of Productivity in a funny way.
In 2017, IIC organized his solo exhibition at Indian Cartoon Gallery, Bangalore (January 7–28, 2017)
Suryodaya Ki Dharati Japan Se, After returning from Japan, wrote a weekly series of articles, published in Punjab Kesari, Jag Bani and Hind Samachar. 10 episodes of articles were a kind of his experience as well as a travelogues : 1997
Kargil Kartoons, During the Kargil War, with the involvement of seven other leading cartoonists, compiled a collection of cartoons dedicated to the Indian defense forces: 1999
Laugh as you Travel, on the occasion of completing 150 glorious years of Indian Railways a collection of 50 cartoons made by Kaak and Shekhar Gurera: 2000
Je Suis Charlie : Lead the group of Indian cartoonists in drawing cartoons to show solidarity with the victims of the attack on French satirical paper Charlie Hebdo at the Press Club of India in New Delhi, India, Friday, Jan. 9, 2015