An elastomeric component for use with an earbud headphone and for positioning within an auditory canal of an ear, the elastomeric component comprising: a distal end configured for insertion within an external portion of the auditory canal; an at least substantially hollow stem region extending proximally from the distal end, the hollow stem including at least one connection feature configured to interface with another component of an earbud headphone to removably retain the elastomeric component thereon; and an outer portion extending proximally from the distal end and at least substantially surrounding at least a portion of the stem region, the outer portion including an outer surface having an at least substantially circular cross-sectional shape in a plane perpendicular to a central axis (A c) of the elastomeric component characterized in that the outer surface of the outer portion having a cross-sectional shape in a plane comprising the central axis (A c) of the elastomeric component, the cross-sectional shape including a concave portion proximate the distal end and a convex portion located distally from the concave portion, and wherein: the outer surface of the outer portion has a maximum diameter (OD max) located a distance (d) from the distal end along the central axis (A c), the distance (d) being between about fifty percent (50%) and about sixty percent (60%) of the maximum diameter (OD max); the outer surface of the outer portion has a diameter equal to or less than about seventy percent (70%) of the maximum diameter (OD max) at all distances from the distal end along the central axis (A C) equal to or less than about twenty percent (20%) of the maximum diameter (OD max); and the outer surface of the outer portion has a diameter equal to or less than about eighty-eight percent (88%) of the maximum diameter (OD max) at all distances from the distal end along the central axis (A c) equal to or less than about thirty percent (30%) of the maximum diameter (OD max). a distal end configured for insertion within an external portion of the auditory canal; an at least substantially hollow stem region extending proximally from the distal end, the hollow stem including at least one connection feature configured to interface with another component of an earbud headphone to removably retain the elastomeric component thereon; and an outer portion extending proximally from the distal end and at least substantially surrounding at least a portion of the stem region, the outer portion including an outer surface having an at least substantially circular cross-sectional shape in a plane perpendicular to a central axis (A c) of the elastomeric component characterized in that the outer surface of the outer portion having a cross-sectional shape in a plane comprising the central axis (A c) of the elastomeric component, the cross-sectional shape including a concave portion proximate the distal end and a convex portion located distally from the concave portion, and wherein: the outer surface of the outer portion has a maximum diameter (OD max) located a distance (d) from the distal end along the central axis (A c), the distance (d) being between about fifty percent (50%) and about sixty percent (60%) of the maximum diameter (OD max); the outer surface of the outer portion has a diameter equal to or less than about seventy percent (70%) of the maximum diameter (OD max) at all distances from the distal end along the central axis (A C) equal to or less than about twenty percent (20%) of the maximum diameter (OD max); and the outer surface of the outer portion has a diameter equal to or less than about eighty-eight percent (88%) of the maximum diameter (OD max) at all distances from the distal end along the central axis (A c) equal to or less than about thirty percent (30%) of the maximum diameter (OD max). the outer surface of the outer portion has a maximum diameter (OD max) located a distance (d) from the distal end along the central axis (A c), the distance (d) being between about fifty percent (50%) and about sixty percent (60%) of the maximum diameter (OD max); the outer surface of the outer portion has a diameter equal to or less than about seventy percent (70%) of the maximum diameter (OD max) at all distances from the distal end along the central axis (A C) equal to or less than about twenty percent (20%) of the maximum diameter (OD max); and the outer surface of the outer portion has a diameter equal to or less than about eighty-eight percent (88%) of the maximum diameter (OD max) at all distances from the distal end along the central axis (A c) equal to or less than about thirty percent (30%) of the maximum diameter (OD max).