About Us

Cook, Downing & Underwood is a well-established, family-owned independent insurance agency. We are located one block off the town square in Glasgow, Ky., and have been in the same location since 1933.

We are a property and casualty agency representing multiple insurance carriers equipped to handle insurance needs including personal auto, homeowners, boat, motorcycle, RV, antique/collector vehicle, life, business, commercial auto, umbrella, mobile home and bonds.

We are commonly known as “The Friendliest Agency in Town.” Stop by our office at 217 South Green Street and let us show you our exceptional service.

Cook Downing and Underwood Insurance
Buddy Underwood, Agent, Owner - Cook Downing and Underwood

R.D. “Buddy” Underwood, CIC, Owner

Buddy has been a licensed agent with Cook, Downing & Underwood for more than 35 years. He has held the professional designation of Certified Insurance Counselor since 1981. A lifelong Glasgow resident and graduate of Western Kentucky University and Glasgow High School, Buddy’s civic involvement includes serving on the board of directors for T.J. Samson Community Hospital.

He is additionally a commissioner for the Glasgow Water Company, a deacon at Glasgow Baptist Church, and an active member and past president of the Glasgow Rotary Club. He also previously served on the board of directors for the Glasgow-Barren County Chamber of Commerce. Married to Anne Grant (Downing) Underwood since 1971, they are the parents of two grown children. In his free time, Buddy enjoys walking, RVing, spending time with his three grandchildren and rooting for his alma mater WKU Hilltoppers.

Josh Underwood, Agent - Cook Downing and Underwood

Josh Underwood, Agent

Josh has been a licensed agent since 2009. A Glasgow native, he is a graduate of Glasgow High School and Georgetown College, where he majored in communication arts. Prior to joining Cook, Downing & Underwood, Josh served as sports editor and managing editor for the Georgetown News-Graphic, a community newspaper.

Josh is an active member of Glasgow Baptist Church. He is also an active member and past president of Glasgow Rotary Club and a past board member of the Glasgow-Barren County Chamber of Commerce. Josh and his wife Sabrina have been married since 2010 and are the parents of a daughter, Callie.

Debbie Rich, Agent - Cook, Downing and Underwood

Debbie Rich, Office Manager and Agent

Debbie is a licensed agent and has been with Cook, Downing & Underwood since 1997. She currently serves as office manager/agent and is a ray of sunshine in assisting our customers. An Edmonton native and graduate of Metcalfe County High School, Debbie and her husband Robin have been married since 1975 and are the parents of a grown daughter.

Debbie’s hobbies include spoiling her grandchildren, Jake, Khloe and Eli, eating seafood and chocolates, relaxing at her koi pond, and doting on her dogs, Koko and Harley.

Anne Grant Underwood, Agent - Downing and Underwood

Anne Grant Underwood, CFO and Agent

Anne Grant is a retired elementary school teacher. She became a licensed insurance agent in 2006 and now serves as chief financial officer/agent for Cook, Downing & Underwood. A graduate of Sullins College (Va.) and Western Kentucky University, Anne Grant is an active member of Glasgow Musicale and Glasgow Baptist Church.

Married to Buddy Underwood since 1971, they are the parents of two grown children. Anne Grant adores her three grandchildren, Anniston, Asher and Callie. In her free time, she enjoys playing with her golden retrievers, Beamer and Abby, tending to her flower garden, camping in her RV, and crocheting.

Beamer, Staff Member & Mascot

Beamer, Office Mascot, Non-Licensed

Beamer is a mature golden retriever who became a member of Cook, Downing & Underwood's team when he was adopted in 2009. In his prior life, he was a show dog and stud dog. He also is a certified therapy dog. Beamer is retired but comes in by appointment to gently greet clients.