Today, the datacenter ecosystems are fueling the demand for novel transmitter (TX) technologies complying with the off-board, on-board, and chip-to-chip computing needs. This has set a new class of requirements for the TX infrastructure that should now offer multiple credentials, namely: high-speed, O-band operation for avoiding dispersion compensation in long distances, wavelength-division multiplexing (WDM) capabilities for higher throughput and multicasting/broadcasting support, and tight copackaging with low-power electronics. Silicon (Si) photonic TXs have been extensively studied toward high-speed and WDM TX engines targeting mainly C-band. Only a limited number of Si-Pho O-band TXs have been reported, however with ≤32 Gb/s/channel line-rate capabilities and with a WDM portfolio that has not been fully explored yet. In this paper, we introduce a novel silicon photonic high-speed O-band TX hardware platform that can meet the current datacom and computercom interconnect requirements. We demonstrate a ring modulator (RM) based four-channel WDM TX at 4 × 40 Gb/s non-return-to-zero (NRZ) operation that supports wavelength parallelism in unicast operation but can also pave the way toward WDM TX engines for the post-100 GbE TX era. Moreover, we present a broadband Si Mach-Zehnder modulator employed in a WDM modulation scheme of 2 × 25 Gb/s NRZ signals and demonstrate multicasting when combined with a 8 × 8 passive arrayed waveguide grating router (AWGR) wavelength router, addressing the broadcasting needs of traffic usually encountered in cache-coherent multisocket settings. Finally, we further demonstrate the tight synergy of O-band Si-RM modulators with high-speed CMOS electronics, presenting an RM-based TX assembly prototype employing a fully depleted silicon-on-insulator CMOS driver, delivering 50-Gb/s NRZ operation.