He released his first CD, Conversations With Inanimate Objects in 2005, and his first television special Gary Gulman: Boyish Man the following year.

[4] Gulman has described himself as a sensitive kid who enjoyed making his friends laugh, drawing and painting, and playing basketball.

[6] Gulman credits the time he spent playing football in college as one of the main reasons he recognized and began to seek help for his lifelong struggle with depression and for his later pursuit of a career in comedy.

[4] He then began working as a substitute teacher, where he was well known for trying out his stand-up routines on high-school students before bringing them to the stage at night.

His second Comedy Central special aired on December 8, 2012, called In This Economy?, followed by It’s About Time in 2016 on Netflix and The Great Depresh in 2019 on HBO.

[15][16] In early 1999, Gulman began to pursue stand-up full time;[17][16] he moved from his family home in Peabody to Los Angeles where he had received development deals.

[18][19] Gulman performed his first late night stand-up set in 1999 on The Tonight Show with Jay Leno.

Gulman first came to national attention in 2003 when he was a contestant on the second season of the NBC reality-talent show Last Comic Standing.

During this period, Gulman performed stand-up on The Tonight Show with Jay Leno (2005), Jimmy Kimmel Live!

In April of that year, he performed for the first time on Late Night with Seth Meyers and in June 2014 he was the guest on The Pete Holmes Show.

It includes conversations with his wife Sadé, his psychiatrist Dr. Richard Friedman, and his mother Barbara,[26] who asked "if Judd Apatow could make her look thinner".

[27] Gulman has stated he had "retired from life" because of his crippling depression for more than two years before recovering through treatment and medication.

[27] However, he felt very anxious and sad when he got back on stage, and his way of dealing with that was to joke about it, leading to the idea for the special.