Oleg Vereshchagin was involved in sports since childhood, including martial arts. During his school years, he began playing KVN. The beginning of his KVN career turned into a comical incident - in a sketch where he parodied the lead singer of the group "Masha i Medvedi", he got tangled in a woman's dress and fell right into the audience. Later he played for the KVN team of the city "D'yavolyata". After school, he entered the Perm School of Economics, but after graduating, he did not work in his profession. Only later did he work for a year at a Perm brewing company. Since 2001, in Perm, he played for the combined team of Perm and Dobryanka. Then he became a member of the KVN team "Parma", where he found a partner for humorous dialogues, Gavriil Gordeev (who became known as "Gavr"). At that time, Vereshchagin acquired the nickname "Bobyor". The team "Parma" existed until 2005. In 2002, he wrote the script for the series "Zagadka Starogo Kladbishcha", in which he later played one of the roles. Together with Gavriil Gordeev ("Gavr"), he participated in the first season of the program "Smekh bez Pravil" on TNT.

There they were noticed by the creators of Comedy Club. From 2007 to 2012 - resident of Comedy Club. The duo of "Bobyor" and "Gavr" became one of the most popular in the show. They opened a branch of Comedy Club in Perm. In 2012, their duo broke up - "Gavr" took up producing. And Oleg Vereshchagin performed in the company of Garik Martirosyan, Pavel Volya, and Aleksandr Revva. Since 2013, he became a resident of Comedy Woman. His miniatures with the show's participants were consistently successful with viewers. According to Vereshchagin, he does not experience any discomfort working in a female team. Oleg most often played the roles of alcoholic husbands or tyrannical spouses. His duos with Ekaterina Varnava ("Muzh vygnal zhenu iz kvartiry"), Marina Fedunkiv ("Taksist i p'yanaya passazhirka"), Maria Kravchenko ("Roditeli rugayutsya posle dnya rozhdeniya syna"), and others became interesting.