This paper describes the use of a parallel discrete-event network emulator called the Internet Protocol Traffic and Network Emulator (IP-TNE) for Web server benchmarking. The experiments in this paper demonstrate the feasibility of high-performance wide area network (WAN) emulation using parallel discrete-event simulation (PDES) techniques on a single shared-memory multiprocessor. Our experiments with an Apache Web server achieve up to 8000 HTTP/1.1 transactions/s for static document retrieval across emulated WAN topologies with up to 4096 concurrent Web/TCP clients. The results show that WAN characteristics, including round-trip delays, packet losses, and bandwidth asymmetry, all have significant impacts on Web server performance, as do client protocol behaviors. WAN emulation using the IP-TNE enables stress testing and benchmarking of Web servers in ways that may not be possible in simple local area network (LAN) test scenarios.