James Baron Cryer, 84, of Leonardtown, MD, died on Monday, March 17, 2025, at St. Mary’s Nursing Center in Leonardtown, MD.
Jim Cryer was born on May 8,1940 in Leonardtown, MD. Except for a brief Army deployment to New Orleans, LA where he met and married Betty Jane Brou, he lived the entirety of his life in the Leonardtown area. He was the son of Alice B Brown and Oscar M. Cryer, brother to Mary Alice and Oscar M. ‘Skip’ Cryer as well as half-brother to Leo P. Klear and Michael Klear. He was father to James Kenneth (Ken) Cryer and partner to Kathy McCullough, as well as dad to the best Bar Dog ever, Bacchus and his successor Trouble. He was also Uncle Jim to Susan Fielders, Jaime Klear, Brian Klear, Leo Klear III, Michael Klear, Marlene Klear, Brenda Faye Bennett, Johnny Harden, Mark Brynteson and Mike Brynteson. He was also godfather to Raymond Michael Digulimio, Jr.
After returning to Leonardtown, Jim worked initially as a car salesman at Fenwick Ford before his foray into tavern ownership with the purchase of the Friendly Bar on the square in Leonardtown which would, going forward, become his lifelong business passion. He later opened and ran the legendary Leonardtown Wharf at the water’s edge of downtown Leonardtown and would go on to also own and operate Dock of the Bay (now Fitzie’s Marina) and Cryer’s Back Road Inn in Compton, MD, which continues to operate to this day. He clearly was meant to be a bar owner, combining a stoic strength of character with a genuinely caring and engaged ear, all the while maintaining a knack for knowing how to decipher fact from BS in relatively short order.
Jim’s most cherished endeavor was bringing together and entertaining the multitude of customers and friends at his well-run establishments, serving up live music and tasty libations which brought so much joy to so many. His “Cryer’s Mardi Gras Queen’s” have become a close-knit and beautiful group as well that help run and ‘make the fun’ at the annual High Summer Mardi Gra Party annually in June. He also adored Southern Maryland Softball and maintaining & tractor-riding on the pre-eminent ballfield in St. Mary’s County, Cryer’s Field, made possible by Loretta and Joseph Vallandingham. He took great pride in the many teams he sponsored that hit the field with his name on their uniforms. He was also proud of the teams of bar staff he put together over the years, some becoming like family, especially our own Donna Breeden. He was inducted into the Washington Metro and MD State Softball Halls of Fame and garnered many sponsorship & other awards over a lifetime of giving. He was active in civic organizations as well including the Leonardtown Lions, Hollywood Moose Lodge and the Leonardtown Volunteer Fire Department. He truly relished being ‘Cap’n Jim’ of his fleet of boats over the years including ‘Frank’s Folly/ Mardi Gras’ and the ‘Bacchus’ and taking friends & family out for ‘cruisin & fishin’ trips, especially on beautiful Potomac River Sundays to Coles Point Tavern & other stops. He took great pleasure in driving his ‘77 Corvette with the top off, eating oysters, crabs and Popeye’s fried chicken & red beans. He specially loved hearing some good brass band music and attending the annual Mardi Gras in New Orleans where he hosted his ‘Cryer’s Balcony’ for parades there for nearly 25 years, his only real vacations.
A Celebration of Life gathering for Jim will take place on the morning of the 85th anniversary of his birth at a spot he held dear, Leonardtown Wharf, on Thursday, May 8th, 2025, beginning at 9am. This will be followed by a traditional, New Orleans style Brass Band/Jazz Funeral procession through the town square to St Aloysius Cemetery for a Christian burial. The procession will return to the Wharf post-burial as well. Parking will be available at the Leonardtown Volunteer Fire Department’s Carnival Lot and shuttle Trolleys will also be provided to and from the Wharf area and cemetery as there will be no personal vehicles permitted in the procession.
Serving as pallbearers will be Brian Klear, Michael Klear, Buddy Tippett, John Tyler, Willie Watts, Leo Cecchini, Dale Wince and Raymond Michael Digulimio, Jr
Honorary pallbearers are Charlie Breck, Ricky Rice, Lou Morgan, Lance Pierce, Michael Brynteson, Harry Pool and Jimmy Fletcher.
Memorial contributions in lieu of flowers can be made to the Clements Cuties Foundation, Second Hope Rescue Inc and LVFD Auxiliary.
His celebration of life will be continued at Cryer’s Back Road Inn at 12:30pm. Please join us for a toast to a life well lived.
Condolences may be made to the family at www.brinsfieldfuneral.com.
Arrangements by the Brinsfield Funeral Home, P.A.
